A guide for the perplexed organic experimentalist

Sou, cea of Valu e for Compound Searching This work, published forthelast lOO'UUbytheMerekCo ., of mainl· me... Compoundsarc1tilllinedonapurelyalphabeticalba,i1,wi1h stmcturC$,phy$ical p

Perplexed

Second Edition

JOHN WILEY & SONS

Chich~ste Nw YO<~ Bri1 e SingaPOre SALLE + SAUERLANOER

AHau Fr1nkfunam Maln Salzburg

0110.S.OII, V""' o ~tt 4Co Fran>luro"'" Vnla1 S.01>«11n<!ttAG,A>" • NQ, ,1ofthi1bool<n>a1 bcr<p<odoe<d~IO·ffi nl, or1<0n1m111<d.or",n.ta1<d i"1oama<b;,,, 1an, ,,

"i!hoot Ibo wrill"' , m~s\o<luf1h< JNblill>«

I On Surohln1 lhf Lllfrl.!Ut Th• lmpoMIRI SourttJ U1ln1 You Hn d

? On SHrchin1 th• Uttrlture-U,fn1 th• Compu1u (and VourHnd)to RttritvoSU\lctur<1, Rdorenon, Ruot101111nd UoH Onlln•

9 g:.:;~~r<>&rulloo-Tltt Cindr«U of lhr 0<1nk

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The perplexed o•aanic cxpcrjmcntalill i,in mynpcriencethc rc,earch worker Hci s !heoncwhocarlyon discovcntha! he hasro11andonhiso•1 n tl'o'Ofttt,in1hcta1kof1urchin1for informaiiononhis subjec1andi n a!lthc prac1ical asJ)«lsof his howtochooscandacq11ircthc tooblndma1erial1ofh ist radc Alltoooftcnit isnotbychoiccrhat hefindshim!<lfin thi, situation Hi1 ,upcrvi,or(or.morcp01i1el)', hi s 'Scnior Collab-ora1or ' )wa,him,clfonccagraduatc1111dent andpon-doctoral researcher But in the majority of ca.« he has Ions since 1ra1ion,withwricin1andrdcroein11rcscar-hgran11pplication, proceuhewillhavefor1101tenmostor1hcprac1icalknowled&•

~omeunawareoflaterde,·elopmcnn

Thea,erqe&raduateSludentisill-preparedfor ><archinat hc Uteraturc.Mostpracticaltcxtbookswillha,·edoncliuletotrai n preparative work on a,malJKal<, and fcwcr1till for workin1 Nonc,1nfar as ! know,doanythi11ito auiitliim(orhiiiupcr-

•iror)101rapple wi1h indi tferon< Jupplieu, manuflc turer, and admi niftratou

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1hal orpnic chemistry i• an experimental science ~m and foremos1, and 1ha1 in the &nal ana!ysis-wi!h aU of modern insm,mentHion and computedsil!ion-it ii 1he organic indispensable Hence there is linlc on inst rumental

s ~trosco pkand a nal)'1ical1 echnique,andotherspecialfiel d,, whichare qui1e adcquatelydea.ltwith elJCwhcre Thcimpor1am matterof,afetyis, with r<gr<t,touchtduponon!yinbrid; to dop roperjusticctoitwouldbebeyondthescopeof thisbook

~nd comparati"<IY linle of ,pecial relevance to them Otheu will nodoubttakee~cep,iontoanumberof1tat cmenuinthi, book J shall be happy if their mis1ivings willinducc 1hem a ll

to write asimilarl>ook oftheiro,.·n

l a m indebtedtomanyfriends andcollea1uesforconmucti,e advkeandcri1ici1m, andabo,·calltoProfessorR.A Raphael, 11«athelp,and10 Professor O.J e1er (SwissFederallnS1itu!eof

~:~h~t!!~i: Zu,ich) whoMe hospit ali!~ enabled me to CC! started

Haifa,

Januaryl978

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This«lition was writt en forthrttiood,e onl The fim v.·a,

thatthech.allenaeexpr<sscdin11>cla<tbutoneparagraphor1hc lamentable fact !hat in the 11 years sin« the apl)<'arance of the ~rst edition there has b«n little if any pros.re" in traini!IJ the synthctk orpnk chemist in two essentials, findin1 the info,

mationhe reallynccd1,andu1in1hi1owntwohandsindoi111 what distinaui,hcs chemimy from 1he 01hcr 1drncts, viz crcatinathcobj«tsofilio"·nstudy Thethirdreasonwasthc succcs,or1hefimedition.a ndthcpublishc,'1sugaestion10

v,riteanotheroM

Much of 1hc added material, and al,o some omissions, =

based on commcnu on the first edition, moH or whkh were favounb!e A few quaint excep!ions: the chemi1t, actina u

watchdog(orshouldoncsaywatchbitch7)forafcminil(organ-i twatchdog(orshouldoncsaywatchbitch7)forafcminil(organ-ion, who succeedo<lwatchdog(orshouldoncsaywatchbitch7)forafcminil(organ-indetenwatchdog(orshouldoncsaywatchbitch7)forafcminil(organ-inaevwatchdog(orshouldoncsaywatchbitch7)forafcminil(organ-idcneeofmalechauvwatchdog(orshouldoncsaywatchbitch7)forafcminil(organ-inwatchdog(orshouldoncsaywatchbitch7)forafcminil(organ-ist dispensin& wi1h a condenser in small-s.tale distilla1ion and toinebtiation anddemoralisa1ion in the laboratory

h i, a 1reat pleasure 10 thank Dr E Zall (Laboratory or Or&anic Chemistry, ETH, Zurkh) for the en1husium and , r t use of the Compute, in Information Retri<'Val l am a!ro indebted lo Dr J Schrcibu (ETH, Zurich) for a numbtr of

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Pror C W Recs (Imperial Coll<&< London) for their

of Cambridge UK) ro, fruitfuldiscu n ions

Ha;J<1

OctaMrl989

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The Important Sources Using Your Head

Thisctiap1ercomesfostb«ause1huiswhe,eitou5htlobe.l'llo embarkedup0nbefo,ea1horoughiovcsti&a 1ionofthecurrent looki11Jforinforma1ioni, 1he,·ery fimthin11,you,1hebqinnini cucs, whe!htT In an academic institution or in induscry; and moreoften,hannotyouwillbecomplotel)·unpreparedforthal

lllk

Thedecade1h.athaspa.s sedsinccthefimedi1ionof1hi, book appearedha,see n a nunprecedenttduplosionoftheamountof informat ionpubli1hedin0111;inicchemistry and adjacen1field, l'onunately, ai the same time there has been an impressive dcvelopmentofcomputer-aidedmeansformriovingthat infor· may dtludeyou intolhinkin11ha1 from now on the com puter :1~;1: ~.~~ur v,·ork archinJ the literature There you would Chapi<r2willindttd1uideyouinhowbesttoexploitmodun mnhods of 1nfo,mation re1ricva1, from • number of but by no

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ixriodorcimea1thin11,11andatprescn1 Ho,.,e,1er, yourmosc impor1an1computerbyf1Ui1 11>eoneatthetopofyourspine, entire ftamev.·ork or modem information retrieval is no more you will pardon the expr,.,ion And that hor<e must he fed a,ve,yexpensive

The fo!lowini; sections are meant 10 aive you a

purpos•-oriemed brief overview of a numher of the imponant currently

happen tohe 'online' at thetimeofwritina;ornot, and then,

by a series o f concrete exampltt, how to achieve the goal of gettin111hefullestinformationbyanime11ra1ed effonin,·olvin1 their combined use

SOME GENERAL RULES FOR SEARCHING THE

Th e fim i• the ru~ of Rttrosf)«tivity, or in other word,, ltffl

from the p,=nt and work backward, in time Of cours,;, this acqui,cdbehaviouralpaltern1(infactjus1 as inlc1rni!lllhow10 ski for the first time!), but ii ha1asolid lo11ical basis hcrc ln o•cr9S ~ ofallcasnyouarcn01thc~mtolookforthatspe-cific item of information Someone was lhett before you, and

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him So why not bend\ from the labour, of your most diate predecei,or, to be1in wi1h? lnconcrctctcrm,this meant lookina &rn at th< lo1cs1 availablc 1bmac1, indeJr the molt rec<:ntlyavail able cditionofacollectivewo,k,uchu!kil,1rin's

immc-Handbucl, drr Organi.J<:hcn Chemie (usually «fcrred to simply

u Btilsuin) {with which you wiU soon become acquainted) and the most rcccntlypublishcdre•icwormono1raph Thcs=ndrulc is:Kttpyour eyc,oprn,brow,e ondno/t down You will soo n discover thl! in formation which in the 1hewayside1ather1ha.n 1ttheori1inalde,;tination Many(pe1-h.i)"mrut)import1ntlineiofrescarchande,·enimpo11an1dis-coverieihave1lanedinthi1 way.Butltwill allbeprettyuscln• (cvcnabustkkttorsalcsslipwilldo),to ,,i,ri1do"'nimmt-diou/y.Thc1ystcmaticfilin11nd110rageof1hcincidcn1alinfor-malion you have thus picktd up can and ,hould come aflc,wards and more on that point later Thcthirdroleis10Kno-.,ond0Uowsptt1.Nc,·errcstassured that, havi ng arri,·cd at the desired information your work i, done Keep in mind the follow in1 ponibi\ities: (1) it may be no1tosaymi1lc1ding.Pos1 ibili1y(a)is~Jdomdcliberate More likely it is the re,ult of sloppine,s or the lack of mean, , or time the more likely you wil! encoumcr it All the ,!,a.me, it i,

remark able how reproducible work lasl done in 1he non inmumemation aae can !urn out to be (1hhough it round, ridkulom, one<an ie! a kick out of ~ndin1 that a compound bility (bl is Mmctim« dclibuate but more frequently due to reaction conditions Muchofyou,ownsoo:esswilldcpcndon making up for that Possibilicy (c) is deliberate by de~nition S<iemimare 1eneral!yhoncs1,butevcnwi1hthemth«ci 1 a dif-fcrenccbctwecnthetruth thewhole tru1handnothinabu11he

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cimion of the work ofothe,s ano1her 'for1enin1' to ,t ate whether the yieldquotcdi,ofi1ola1cdmaterialor 'byGLC'

SEARCHING FOR A COMPOUND, ITS SYNTHES IS ANO PROPERTIES

The mo,t frequent object of a litera1urc search is to find out whetheracertaincompo und i,known , how it is belt prepared and what i11propertiu areorappeartobe Here in particular work should start off

Instead of &ivin1 sy1temaiic survey1, tables, i cheme, , etc which •nalyse the most imponam rourc,:, and which you will will bridy describe thne rourcu and the mos1 important prob· lem , andadvamagcs u soei~,cdwilh them, lllld lea,·cthere,1 to 1heExamplC$ at theendofthechapter

Thisisand remainstheuniguelyindi,pen,able ,ourcoofreccnt others 'Recem'hercmeans',incctheappearanceofthc!alClt relcvantvolumc ofHri/Jrcin' (.«below)-assumingyourinsti· Ili,tobehopedthatyou r libraryha, a ,cction ta,ide rolely re,en·cd for CMmical A b,m1c1S and i1 1 perusal, which generally involvo,comultin&andmovin& around, ·oralhoavyvolumcs ,0Jumo o•er loa,othat area cxcoptfor bindin1-no1ovcn for photoeopyin1.1owhich1hcrci1 not much point anyway The mo5t important pan, are the lndexe1: the Colltt:ti•r

fnde:«sinsofarutheyha,eappearcd andth o ,omi·annual one, 1hi1 hasb«nsubdividcdintoth0Chemica/Sulman~/ndrx and

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Wi1h1he apl)<'a ranco andbindinaofoach newCol/«1ivr /ndtxallthoprecodingttmi· tho Author Inda-there may alway, be cho time when you will belooki111for,om<1hingpubli,hodby,o.and-1oin1heycarX

Thero are four main problems encountered by tho \>eainnin11 reiearcher, thosoofnomondature ofovoluatin11thoen1ry,of ovaluatinathe abs1rac1i1i<lf (nownot all1 ha1 , i11nificantl).and sou rctrtferrodto

Herecho aoldon rule is ~o,rguordal/1ht 1imt.1fyouthink tha1 JUPAC nomenclature is now universally accepcod you are own Of oouri< the tver-incmuinc UK of computer ttarching andprintingprovidesagoodrea,on(no11 0,ayexcui<),but that kind or rationale And what complicates matters most is thowaytheyhavei nthe pastchanaodt hoirmind,evorycouplo ofyoan.lfthercisoneindisl)<'l\1ableadvicetoaivo,;1 i1thi,: use the lnd~x Guide~on$tantly It i, tho one inst rumen! that will 1uidc you throu11h the many confusion,, incon,iotende, and in,ongruitiosyou ·moncoumer

The'oasy'wayou1of1he nomencl atu reprodieamontu,ually chos,nbybeginncrsis1olook upth0Formula/ndtx.Tfyonarc lucky youwillhavcsomethinali ko20-)0i,omenwiththcaame empirical formula 10 ,hoott from and d«ide on one whott name loob reasonably like that of the ,ompound you uo lookin1for lfnot,youwillbavoov,:r IOOtomu!lov« Prob-ably you will soon come 10 the tondu$ion that one might u ,,,o11 faccthonomenclatu,ep,oblcmhead-ontol!artwith

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Thi> b wh«e you can save a lot of time by u, 101 your power,

that hundrtd> of people are involved in pr~parina Chtmlc,,I

Absm,cr, and that human na1ure and 1ubjectivi11· play thei r part However, 1here have Men con,iderable improve,nents in

to where a compound wa, indtcd prepared, quoci111 imental delails; previously in many CI J<S it referred to where

e,pcr-it ju•t happt-ncd to turn up as a by-product in minute yield Entries such as 'caI<.inogcnk acti•ity of ." or 'in l["apc

pound' 1 "C NM R ,peccrum, whereas "bond le1111h in '

might Physical propcrties (e.J mcltin1orboili111poinU) are

of ',buttheymightbcJi venor atlcasttherelevantliterature cited in entries referrin1 to 'magnetic susceptibility o f .' Entries suc h as "oxidationof ', 'rcactionwithtribu1yltin hydride' or 'N·prot ectionofpcptide end 1roup,with .' were once au fet>etthatthcrourceinqucstionwoulddescribcorat you will find 11 but that tM compound w11 obtained from !he researcher was on a limited budsct-a matter on ""hkh the lndex i, not lil:clytobe informati•c

~;::~a ting tha Abstra~r and rha Journal /or othfr soorca)

lnthi1sec1ion,jcurnalsare m0$tlyrefcrredtoby thcircommon aiuwcr51os,arche,ue obtained lnthcJoodoldday,,an abmact , callywasanab1t ra1;1 and pve enou 1hde1ailto J<f\"e inmostca1<s a, a,ubS1ituteforthefullpublication.Thoseday1 havcaoneandtheabmacthasbecomclittlemorc thn anothe,

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the,ei, no problem lf l>OI , a, bappen,mort and morc1heff' day,,1hequestion ari<esofwhe1her1otahthenex11rainorbu,

to whertvtr publication• such u Farmaro Ed Sri., Khim Cdlt rosikl S<H<iin or Sb Pr Pedago1 Fllk Ostravt Rada E

know1helangua1e: and knowi nssomronewhod~sand!hen orde,in11copyi,no1 1lway1a,olu1ion Therearefewuperi-enctsasfrumatin1.ur rying1ot ransla!t anarticlein Yakugah

ZalSlriwith 1he help of• Japanese Ucture, in Social

Economics WiihRnuianjournals, howe,·er,animponambul

in EIIJ,lish translation, such as J C.,n Clrtm USSR (Zh 0/Jshch Khim.) and J Orr Chem USSR (Zlr Ort Khim )

An imponam poi nt to ascertain iswhotherthojonrnal i,in the formofacommunicaiion, andif,o, in which journal In

Cht m Commun or Chimja yon are not likel y 10 find much

Tt tralrtdron Lm • J Ort Chem or J Am Chem Soc As far

u tholatteri1conce,ncd,yonwillsoon~nd1hatcenain aut hors pubhshnothin1butcommunication1andonlyecryrare!y1full paper Here 1he prospect of ever ge!t inJ fuller information is not bri1h1 unless the Senior Author is wilting to se nd ii to you aflcr writing to him penona!ly (and when )'OU wrile, do no! for1tt lo chtckwher hertherth11 b«n ac hangeofad dre11from offence of not knowin1that he/ shehas moecdtoamorepres· ti1io us in!l itution or posi1ion) And now even "'ith full papers imenta! detail will b< sc,nt 10 you "' '1 npplememary material' on!yaf1eryouhave ff' ntach«1u•for a trininJ •um, forwhkh the bank maychar1e you morttoproc<ss !han it iswor1h The fact th.a, 1 reforencei, to ajour nal which fromitsli!le

i, not mktly in the or1anic chomimy field need not deter yon Someofthebcstandmostdetailedinformationcanturnup in Journal1 such a1 Agrk Biol CMm Plry1ochtmi11ry J nd J

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onlyna1uralforthem to1ry anddemonStra,etha11heyhavenot los,:.~:• i~;:u: h r:~d : : : ~ : , oo v.·l>ere 1he abstract i1 of a

Pa ten! Library and where the abstract ai,·es no worthwh ile airmail or ifpessible Tele, or Fa assuming you have made sure1ha11heinformationinqu 1ionh u notb«npublishedin

a rca u!ar form, which do happen T urnina up one' , no,c

a utomatica llya1 a patenti1 notjust i6ed;tbis authorcanr«:all anumberofcue,inhis experience"·herein1hepreparationof atrickykindofcomp0und,followina a pa1em a ndno1apaper

of commerdal importance only patcnU ue published and you then have no alt ernative Ho,.·ever, remember the bottom Line inconnectionwithpatents: thcy arewrinenby people whohrst objecth'eisnot publicationofknow!cdae fo, itsown sa ke(or 1he11akina-outof a lo&alclaim-and1huusuallybynot1ivin11

S.lht.it,':, H• ndbuch "-' 0,y.nl~ch.,, Ch;,mit,

There i, probably no1hin1 to comp.are with 1his work in any 01hcrbra nchofscience andweoraanicchemim u cuniquein incrcasinJ doubt, for many of u1 on how much lon1cr we can

is Thc factthati1iswritteninGerman(up101he founh supple, material' written in En11!ilh, includini a alossary of German youinu,in1Bd/sreln, andmos1oti1i,availablefreeonapp!i·

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To summarise, Btils1dn is organised in,o a<,yt lic (Volume, l-4), isocydic (carbocydic) {Volumes $-16) and hemocyclic pans (Volume, 17-27) There once were additional but now (Hauptwerk, H) ha, l>een complimented by 1ddi1ional series onward, the lauer iwo ore combined); and those fou, Comp-lementary Seri•• arc now comple!e 1oi:e1her v,·ith • Formula /,rdexandS11bj«1/ndex.Theu,o,·e,allorsanicoompound1on

year J9j9 , That year is thu1 1hecu1-ajJdattbetweenBtilstt in andChemica/Abslr<Klsa,thing1Handa1pre>em,andhen<0on

Cltt mica/Abstracr, Indexes before che Col/tt:/joe fndt xts for the period 19,7-196! Thi, is assuming, of course that the inthi stesp«1.Aoewcomp1ehensiveGtneral/ndexforall1he>e probably vory adoisablc to acquire this, even bylib,aries who becaustapartfromaivin1 atot1lpicturcofal1thati,knownto morefortunatelibrarieswhi<hcan s1i ll afford1osub1eribe

A M1h , upplemen1 ary ,eries include, compounds on which ioformatioohadbtenpublishcduptoandindudini 1919, and chis i, now in English: however, ,o far this applies only 10 Volumes )7~19 and thu! to hetrrocydes with one or two oxygen The rule of retro,pectivity applie, aJ,o to Btil.stt jn, Each ,cries refer> back with every compound, lo the appropriate page in previous ,cries An impor1an1 aw,iliary ii the Systtm Numbfr allotted 10 each compound and iu homologous and

func!ionalmodificuion, Thi1,:on1jnut1unchOnftdtltrou11tou1

al/serit1 a numl>erofseparatebookJ)

ndhelpsinloc11ing1l>eappropria1ebook(panicu-The areal advantage of compound ,earchina in Btilsttin

ratherthanChtmica/A/Jslro,·/sliesnotonlyinthefac!thacyou

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tudc: not everything reponed is taken for 1ran1ed and later

~~:::•:::e·~~:t~~:::;::a:;;:sf~~ ~:~~!~;~~;~~~:!:~c 11~: tu,e Abo,·eall,&ilsrclni,idealforbrowsing.toanextent neve rtobeanainableinthefores~ablefutureinanonlinerom puter search (see Chapter2) Whu is meant hereisexptoitina deri,·ative,a ndhomoloaue,and ofcour1e, 1h eirprop,ertiesand methods of preparation

However to get the most ou1 of Beilsrein yo~ must know ,he

:;.s:::; e~~ :er::~~ ~~~e~h·:~~::;:!~c::::~; ;~d:~::: add.ortoavoidthefrunrationeausedbythefaelthat a com· hut will be found in the ,olume marked 'Heie,oeycles, JO, Mono· and ?olyoxo Compounds' How ·cr the main poinl is

that there is a system and lhal it has remained practically uncha~ed during then yearsofthework',eJtinencein in present buk form

0 1he • Mino r Sou, cea of Valu e for Compound Searching

This work, published forthelast lOO)'UUbytheMerekCo ,

of mainl)· me<lkal pharmaceu1ical bioloaical and abo general substancesarra!IJ«l throuahout by,erial numbtr lfthecom-poundyouhappentobelookingfori, amon11ho,e lOOOOyou arc in luck bf\,ausc the information i, pre,enled vuy

thorou1hly What you will see are 1tructu re, lUPAC and alternative name,, 1enerk and commercial brand names, evan1rtccntliteratureci1ationort"·o.crol5·indexe>also 1ivin1

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with uch rompound its Chtmko/ Afutnuts Registry Numl>cr (a very important it em for Chaptn 2) All in all for a one-•olume workthisi, arulbar,:ain

Dictionary of Organic Compounds lEd J Buckinghtml ' Thi s ,ucce!l<lr to the former "Heilbron" Dictionar y is un doubtedlyanimprovemenlonitspr«lecessor(all>cilChapterl ,o far appeared in ~ve main and four suppkmemary volumes Compoundsarc1tilllinedonapurelyalphabeticalba,i1,wi1h stmcturC$,phy$ical propertie,(indudin1thoseof1impled0<iva-tive,) and several relevant and comparaiivdy recent li!eramrc refercnccs(fortunacdynow indkatin11,.·hether relatingto syn-1hc!isorto,pec1ralpropertics).Allcompoundsli$1ed(1ndtl>c,c 1u1ion)1tenowgivcn a running serial num\>erwhichmal:esit al1emati,·e name!, the 01her with a molecul ar fo rmula index, a 'hettroa1om'indn(uM'fulwhen,earchin11fora11oupofcom·

Ch~mical Abstracts Regimy Number Index (see Chapier 2) Howe,·er , the basic wukness is and remains the alphabetical arran11ement(i.e.compound,arenotgroupedundorsomeba,k

Chemic,,/ Abslracts or Btilstt in for a thorough comp0und

arch Abo, i1 wi111ake 1he experienced user Jes, than five minutes to find, or rather not find, at lea.i hal f-a-doun

• tall

SEARCHING FOR A METHOD, REACTION CONCEPT PROCESS

Thisi,muohmoredifticultbecau,ethesearchobjec1isbynatutt lest well defined If it is • name reaction (e.1 Reformats ki,

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procedure(sil)faiion, hydroacna1ion)ora.cop1edconccp! task is rolui,dy simple !twill become more and more diflicuh

aJ its designation becomes more daboraieand complex (e.1

Michael.typointramolecular addition - cycli, 1ion, au chroma· toaraphy ofsilylated amino acids, dfc.,t of solvent, on enoli· , tion)

There are two pouible approaches 10 this problem One is 10 take imo account !ha! most such genonl search obi~• can indexcr'sidu,onthi,willfrequentl)·"oedilferemfromyours anditi1 inanycasca Ju1aryandoducationalnerci~fimto lem an "oe formulated But 1his means employin11 your Intellec-tual p0wer, for more than merely changini the order of keywords-anyoldcompu1crcando1hat The second approach lies in examinina how your problem can

be ,plit into component parts, euminingeach soparaicly and

!hen , ,ina how !he rosulu can be imograted For example, when11udyina thcpoHibilityofgcninaproductBfrom,taning material A po"ibly u,i111 • reaction ,uch u Rand a reagent such as X, one can proceed u follows:

(a) look up ,very knm,·n review on Rand ,co if the Tabular Suf'·cy show, anythina likeA u ,1artingpoint andlikeB11 result;

(b) look up A in, for example, Btilst~i~ and look up wheiher it

or homologue,orderi,·ati,·tshaveoverbeen subjc.,tedtoa similarroac1ion(ane,,ampkof'Beils1tin·brow,ing'); (c) look up ll in !he ,ame ,.·ay and , , whtther it or ,;milar oompound•havebot-nobtainodinalikcmanner; (d) look upX in roferen« books de,ottdtorcagcnn and>eo whtther iu use ha, over been usodued with compound, such as Aor B

Natu rally, whichever approach you embark on you will be

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is noted down and ul1imately ~led a,.·ay for rmurc rducncc He,e 1he rule or mrospeC1ivi1y is p.;mkularly importanc A

workerwhohasin1hepa.s1uK<lacompoundinwhkhyouare ime,es,edmaywellno! ha•cbo1hcrcdto 1i•eap,evious <0fcr-encc to i1; bul when ii comes to a1p :ial ly))t'ofreaction or application ofa p,uticular concep1, 1hc,e he cannot &<l away

!herefc rceswil!sec lo that

Wcucdeali11£hcrc with a1y))t'Oflitera1Ure1tarc hwhcre1hc numbuofpotentialsource,-ofinformationis•erylarac Wha1 thcbtai nncr needs issomeguidctuthe most gcncrallyu1tfol 1akcnintoaccount

Thellhelme r'• Syr,th• tlc M• tll(H# of Org• n /c Ch• m ls try ' '

Here is ano1her unique compcndium which, afcer 1enin1 used 1oworkin1wit hit,1hcor11anicc•J)t'•im<'Tltalistwillsoondecide much it com, andhewillbt!dtwondcrinaand"·orryina how scribe co it forty-lhrec•olumc, ha•csofar appcared, almOl't onecachycar,ande,·ery6fthvolumchasaeollectfrcindc,.Th, complaint,cvcn1hou1hoocasio nally1howin1 asubjccti>·eslan1 E,eryeu.mpleJive,-fullmu iures (apparent!y1hcmos1'rost-in1ensivc'i1eminthis"·ork)of,1anin1moted als,in1crmediates

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moll important part ;, _the de1ailed and carefully cros, referencedindcx.Jtise"1"yrarctolindoneins!lncc-,for eumple, whe re a reference for 'A ,1anin1 material for B' wa, indexrcfcntot he Example1'umber1mdnot101hc pa1e.h al,o list• rea1en11 (inorga nic and mctal-or11anic alwa)'' under the types A speci al Guide for usin,g this work hai appeared.'" reaction cl asses which looks rather in1imidatin11 and tend , to fri11h tenofT1he be11inner , butm a.stcringitisnotrcallyc1scn1ial

11 isesumial, howC"Vcr,tosctacquaintedwithit if you intend

to exploit Th t ilhtimt r like Bri/.slt in fo r browsins a nd 1c1ti n1

information by a1sodation, , in-e it 1roup, reactions of the wi1hfuj/sltin)whcrcthefae11hatthi,workisnow available for 'browsabi lity'

Al the end of each ,·olu me1he reis a ,·cryimpor!a n! Table which lim later supplementary reroren-es for eumples 1iven

in presious volumes This must be used with some cart For examplt, 'Vol l 23, VoL 28 JO' mtans that pagt 10 in Volume 28 contains an example or other information which com p!emt nts t xampl~ 23 in Volume I Each volume i, also prefaced by an in1roduction which , um l up special dcvelop-mems1i nce1he a ppnranceofthepreviousone Thebindin1 ofthiswor kused tobe1erri blc (fnrits pric•)- in practicall yeveryl ibrary the aut horhasbetnco Volume 10hai there has becnconsiderab!eimprovemen! inthis,eprd ,

Since1headventofthedivisionof 1heorisinat Subjec1 /ndt x into the Cht m ical Substance Index and the Ot ntral Sub)«t

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it dMs indee<l-wilh wme rcsc,rvatfon, The number of head in11.1 has inc,ea.e<I eno,mously bu!'° has 1he number of encriei Qui!e apart from making thi, hard onOllC'scyC>i1ht ands1amina a lotofcarcfuljudgmuthas tobeut1ciscd,1hc

••=n bein1, as mcn!ione<l before an all-100-frequcnl Here is one example:

differ-The1earchcrmaybelookinaforamc1hod "''hich speci ficall)' effects mera-bromina1ion of phenols In Thtilhtimtr, lndu

of Coll,:,;1ivc Vol 40, he will find: "mna-bromination'-!his refcr,toVol.J.6.examplc474.Thisref«11oapapcrby J C Jaqucsy ti al., Clrem Commun 110 (1980) which show,

that 4-alk yl and 2.6-dialk)'lphenols are brominated ci&calty in !he meta position when di.,ol,·e<l in HF-SbF,

,pc-('1upcr-acid" ) Thei/htimtralso 1ta1e,: 'd Tt lrahttiron 31

747(1981)',meaninachatthereoncwil!findadditionalinfo, malion !n Chemical Abstracts, on,heolhcr hand(Genen,/ Su/Jjrc:1 lndtx, CoUtt:tivc Vol 1977-81) th< followina si1u-

a1ionis cncountcre<l:under'Pheno!s,Re1ction,'oncwillfind 'bromina!ion', but not 'meta" nor ncn 'reaiosl)fcific', but one w/11 find 'bromin ation of in super-add, mecha ni,m or (93 94918a), "'·hich i, found 10 refer ,o the at>ove Chem Comm~n p;ipcr-however lhett is no mention of 'mt ra' or

of the Tt l!ahedron pal)fr On 1he other hand, unMr

'bromination"onc willfind'mt/Q', but now!his i,qualified: rdcrsonlyto9S,80l47t,whichistheabmac1ofthe TetrQht-

dronp;1pcr

Thi, isthew,tofthinathatha pl)fnsallthetimeinasu,ch

of this kind in Chemical A/Jsiram, but that 5hould not nc«uarilypu1youoffcon1ultingi1alto11.e1her.Ther<arc

:;,~; ~~i;~ is mi,.ing from e.g., Tht ilheimt r to make ii www.pdfgrip.com

Thi, work, !4 volume• of "· hich have apP<"ar«l so far, delivers far more than its title would1uue<1, 1ince it i,1he work in which to bnd imponam and uwto-daie information by browsin1andassociation,but !henonlyifi1i , readandn01 opinio n, it is probably the best 1inglc investment an CXP<"riment alorgankchemis1canacquire a11hepre1enttlme h

deals alphabetically with reaaents u,«l in or1ank chemimy, wherethoycanbebouaht, ondineachvolume referenceismade 1eneral index and more imponant, an 'Index of Rt<18tntr

A<:<:ordinz toTyfHs',"·hiohineffccti,1nindextoreac1ion1and methods The only snag lies in 0tta1ional and unexpcct«l chan1csinnomendaturefromone,·olumetothenextandeven

in the ume volume betwten the index and the tul to whic h il

refero Bu1wi1ha,.·ork likethisitmayevcnbe a blessi111indis· 1;uisc, since puttin1 thismai1h1 m•ywcll put you on to more

unexpected1crn1o rinformat ion bythe ·ay,idc

M athoden dlr Organ/sch.,, Chemif (Houben-Weyo • Thercis a loltha1need,tobeHidaboutthi1elephan1inework compounds,1heirpreparationand,eac1io11$ Forth•beainnin1 lows: m11Ch of it i, not easy to use, to put it mildly; 1o mc of it i<cxcellemandwellworth ma kinJ thccfJon of acqu1iTitance

Up to the most recent volumes one had hm of all to dedpher 1hefine1oldleucri111on1hchackorwhat wulcr1ofi1, 1u which of ri,·e or ,ix ~o!umcs (all mar ked for exampk 'oxy1cn phoro1nph of a Vuy Jmponant Peuoo, skip throu1h 2-4 throuah 14 pages or more of journal abbreviation, before

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one hu co cope wi1h fiendish new-ny~ indc~cs that mention basic mucturcs but 1ha1 arc woefu lly short of listing more aencral topicsandconccpt1 Asforthe ac1ualcontents wmeof the newer volumes a rc supcrh (c.1 thoso on orsanometallic 01heuarejuttplainawfulasfaraslcvelandco,era5euecon handandof11eneralprinciplesofcons1ruction-inthi1re,pcct

Hou~n- Wql althoua h also a German work, is the anti!h«is

of Bt ils1ti11, No wonder this work is almost ignored outside German-,pcakin1 coumrie,, which in some ways is un fo rtunate The Ex<lmp/tJ 1ivcn at the end ()f tho chapter will so,rve 10 amplify w me of the oommCTits made hc,e O'fll!nlcRucrlons

This old-cs11bli1hed ,cries C()llcetin1 review, on 'na me" reactions1nd01hcu ofaweildefinedcharac1cri1pcrhapsthe best kn\>wn of int)'])t Each suchroviewhassection,diocu.,in1 mochanism,soopcandLimitationsoftheruct iondiscussed,buc ofthel'ewill1n,,.·erthecard inal quc11ionincverycasc: how a environment and/orinthcprucncc\>fo1hcrfunctional groupi this occas ionally borders on the incredible, such as the 11<·0 author re,iew on the Aldo! Reaction (Volume 16) which lim a totalof 23S9 rdcrenc

The !\>Ill number of volumes has now reached 36 but itis unlikolyrhatyou canoonsidor any o f,hc ch apton publishedin

(he &,st 20vol umel'ascon.citulinJ any1uidc a1 1lltoprcsent kno1<·ledaeof1hesubj«1 For any subjoctdeah within 1h""' below, ' On Reviews in General' ) which in all likelihood you will

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find You may even find rep<at revie, , in OrsankRractions

1hem,elve1(e.11 Rcformauki reaction, Fluorination) lfyou do documented current inter t ,ueh a, m<1allation Ouorination, directedaldolrondensation,oruseofalk)·nylaluminiumcom, pounds,thenyourfirstscep,houldbetotake advanta11eofthe fact that there is a r«ent Organic Reacric>ns chapter on the

subjectand1ha1themos1r=ntreferencesqumedthereareby Autlior') at the present time

Comp,.h•nsl~• Org•nic CMmistry IBanon and Olb) ••

The best overview of !he state of or11anic chemistry as of I~

~ 1 innln1 ofthe J9(/(Jsi sprobably 1i,·enbythi, work not least fo!lowina:Formulae,Subjecu{bolhclas>esofcompoundsand individual compounds mentioned), Authors, Reactions (in-cludin11 references lo the most imponant recent reviewi;) and Reagents The work as a whole thus suppleme nu and even sup·

at present-the question is, for how much longer?

Org• ,,icSyntht>sa,

Th;, well known collection has bee n left here until last fo r a i:oodreason, whichapplie,particularlytothe fim fiveCollec· 1i,·eVolumes Theveryfact1hatitcon1ainsd01 ailcd andp.ains· closely related one1 in it,elf performing a 11ea1 ser•ic• to organicchemistsasawhole.canbe ap1yrhotogicaluapforthe beginnint re>earcher He i, templed 10 believe that directions canbeapplicdverbatimtomaki141another aromatick01oneB

on a molar scale are ,u itable for maki141 a millimole Fonu· nately,themorerecentj1suestake a widuviewwltheachspc cific example, d iseussscopes a nd limilationsu,d tend to 1ive

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manycuesha,enot publi,hedelscwherc

Theproblcmisthatthereareromanyofthem.andhencethe howiocon,u ltandevalua1e i1 Fonunately,therearelndexes index.notmerelyofreview1perstbutofanypubli calion1hat mi5hl be construed u havifii review character, i, the semi-annual fndtxofSdtmijicRt viowspubli,hed bythe!Sl(ln<ti-

iute for Scien1;fic Information) This may not be found in many librarics.b ut aspanofathorouahliteraturol-(architiswonh are that published by the Royal SocinyofChomislry (RSC), whichhub«n updatedSC",·eral timcsinthcpa,c bu1not ,~ry recently,andthatappcaringatthebackofeachissueofthepcr-iodicalMtrhrxJsinO,ranicSyn1hcsis.1Jsopubli,hedby1he RSC 1111d which should be cOm'Ulted on a routine basis The samekindof!istusedtoapp<arp<1"iodicallyini1sue,oflowrnal

of Organic Chrmistry, where it bcne&ted in panicular from an

:::~::~::;i-in& ke)""'Ord inde~; unfortunately thi1 hu been dis

A «view is of course where someone else should have done 1ll thcworkofcollectinginformationforyourbcneh1 lnprac· understand why, by knowin,somethin&of!hecircuoutance, under which most re,iew1 are wriuen To1hi1 end one could divide rc,icw, rou&hly into three categories Jn !h< ~flt are 1hosewhoseauihors were rcquiredtoco,·e,a 1ubjocte<1mp<e· hen,ivcly up to 1he time of writin11 Obvious •~amp!es are 11,o1,(

a pP<"Uing in Or1onk Reactions and Chfmira/ //.reir ,s Pans of

"ries such u Thr Chrmistry af Functional Groups," Tht Chemistry of Htttro<:ydic Compounds" and Or,(mic

11bclon1ina101hiscate1ory

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Tho ,ocondgroupincludo,tho,oro•iow,inwhichco,·eragoof

a 1ubjoct wa, done for J limilodpcr iodoflimo Thnc'can be found in >0ri• ••uchas Annu11/Reponsand SJ]«iulisr Periodic,,/

Rrportsfrom tho RSC(manyofthe!anor now discontinued),

and in a largo number of other ,;., usually prehed by 'AnnuaJJl.eports ','Pro5ro in .'or 'Fomchrino '.lnmost thorough,atanyratefo1thopcriodinque1tion,becau,e1ho prepared for thorougl, and 1y,tematk ,cannini of the ~old Tha1iswhyreviewsof1hii kind,con1ainin g themostsianificam earliorreforences,willprobablygive1hebes1ovorallpicturoof 1heprcsoms1ateofknowled11oinany1ubjec1co•ered The 1hirdcate1oryare1hoiewhoretheau1horhadbeon wor~in11 intensi•ely in his field, had accumulated many litera-turoda1a and hadcomc totheconclusion1ha1 he had I con1ri· bution 10 make (and/or ~wan opponuni1y 10 enlarge his publicationlist) halsoincludestho,ecase,whoro hewa,con· sideredbyo1hers1obealoaderinhis chosenorsolf-o,iainated field and was !hen invited 10 write a review with no min&• anached Naturally you will find1heropar!icularemphasi1 on which hcconsidored tobernostrelesam(ifno! affirmuive)lo

hi, own Such re•iews will ofltn be found in seric, such H

Acrounts of Chemical Raurch, Cht mic.,/ Sodtly Rtvitws

(formerly Qu11r1,,/y Rt >'itws) Angtwandtt Chtmit lllld in

journ als,ucha1S}·mhtsis, Te1rahtdron,Bu/lrrlndtlaSoclttt

Chimiqut dr Frunet: and O,gani<: Pffp,,rati<ms and Procrdurts

Whathadbestbe idabouca, iewofthi,1)']>tis tha1anyone lOlal number should betrea1edwi1h re,orve

Reactions, method , and concepts usually become a"ocialed wlth1henameofwhoc,serhasbttn consideredtohavccontri-buted mwt to these (sorne1imes unjustifiably so) Hence it 1tands1oru,onthaty<iucangel more, andup·IO·dllo, info,

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tieular ifhe/,he i,,tillalive ind active ThoAurho,/lidtxof

Chtmi~al Abstra~ts i, the ~m place to look, but fml of all one hasto docido><'hichnamctolookoutfor Therei,1heprobl<m

of nam e duplkation-you will be amazed to find how muy chemiststbetoa,earounde,·onbearinga namethal i5uncom-mon; andevonthccunomaryrequc,1madcof au1hor1that 1hey supply a1lnst1woini1iaL<(whethertheyexinornot)doc,nol right name there may be another problem Until recemly it wu n01 clear from a pa~r authored by, for instance, Pickle,, Chu1neyandGherkinwhowastheseniorau1horandhencethc 20on,ries for Chutney and only one for each ofthcotbcr1-obviou,lyChu1ncywas yourman(orwoman).Thisapproachi1 no\ quite foolproof: Chutney may by now be o,er 6$ and

s~ndin& mos! of his/her time on commi11ce1 or tra,·elliq from oncmectiltitoanother,anditisnowPickleswhoisnowpul>-lishina (or ~,i,hilti) in • junior po,ition Quile likely it i1 he/she who ;, now following up the oria:inal idea Nowadays corresp0ndencc should be addrmed' In most cun thil is indeed ,he senior author nnlcs, he/,he doe1 no! ,.·am 10 be 1uchreq ue11Jaremoti'ltodbygeni141the.iam1» onthecn•c-lopc rather than the leamedmate, jalinsidc Youwillha•enoticedhow1hispar1icularparaaraphha,been careful about the lex problem Wi,h ladi<1 therei, thcaddi· tional problem of 1he chana;e of name on marria&•· For example, who6mpubli,hedin l948underthenamoofM.Robcno

Ch•mk•I A bsu•cra Key Word lndu

Every w~kly issue of Chemical Almroc11 now cont ain, this index which alphabetically lilt! combination, of 'keyword.$',

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keyword.Jar• as,igncdbytheindexcr ond ofcourscigno,e entitled 'Preparation ofl-Acyl lndolc, Tricthyl O,thoa~tatc and TlimcthyJOrthobcntoatcasEffccti•cAcylating Agents' is referenced in the Kcyv,ord lndexbyfoorentriHa, follows· Jndo/e-acyla1iononhoaccta1e onhobcnzoa1e Acjiallon - indoleonhoace1atconhobcnzoa1 e Onho11ee/al -1ricthy l indo!oacyla1in1 ascnt Otth0Nnzoa1 -trimethylindoleacyla1inga11ent This index i, byno means a vade mtcum for following up

c,.·crythini; hapixnin;in the 6dd in which you a,eintcre,tcd (ha•e)chosentoputin1otMtitle andJ01wha1thc abmae1 or incomplete.Forinst ancc,byri1htsinthc cnm p!e&ivenabovc thcre,houldhave'oecnanotherem,y: fndolt-3-ac)'l ,nc.,but 1h creisnot.l n othcr"·ords, 1hcKcy"·ordlndcx,houldbe ,cprdcd a, only one of the many d., ice,you should use fo r

kecpina up-1 0-date

Thi1i1 thcco llcctivc namefor1n um berofindc,cs publi shcdon apcriodica l basis(usuallyqoartnly)bythc lnstitutcofScicn-ti&~ In for mation (IS!), already mcmioncd as publisher of the

Index of Rtvitws There are ihree main part! The Sour« Index

list1alphabetically1hcnamesorau1horsando1hersou,eeswho ha>·e publishedinthcpcriodunMrr., icwandgi>·cs 1hc!i1le, and loc11ion of their publication, The Ptrm~u,m Inda Hsu

' subje<:ts'(•cebelow)andcntcrs1hcnamcof author1 whohave publi,hcdmmethanon~onthesubjcc1and1hosewhohue publishcdonthcmuniqucly.Thi,index,houldno1becon-1idcrcd asequivalen1101heChfft!ir:al Atmrac1sone-unlikc in

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only Ho,.·ever, for the pranisin11 o,,anic chemist 1he most impo11an1 by far i,th< Cilarion/ndu

In recent )'Cars it hfl< been difficult, mon!h by mon!hor e,·en w«k by "'«k not to find any issue of a journal in orsank chtmistry without rome publication describing• synth<'lic method or reaaent, that doe, not Ia)'daim 1oa superlative of '!h< fim time that ." o• 'the on!yonc that bo!h and ' Moreoften1hannotourperplexfflchemistwill discOYtr thllt applicat ion tohiscase undert heconditionscitfflgiYe,either ttroorvery lowyie!dsorleadstodi!Terem results altogether The~rtkularirnport anccofthcCi1a1ionlnduin1hi,,i1uation liesin1he"·ayit enable,onetofindou1whato1her••orke'1'' cation, especiallyas thisindex(whichappears"·erylmomhs)

is one of th• most up·to·dat< secondary publica1ions now avai lable Witholde,,.·ork,, :entau1horldo,howa1tnd•ncy n011ocite,whetheroutofncaligence,forgetfulncs,orfromless so,where,·crcom mentis appropriate,whe1 hcr i1bepositiYe(i.e confirmi nithemigi nalfinding),nciati,·e (reportinathatitdoes notwork orworksbadly and1henofcoursedcscribinaabelter was worked out) Thi s is where followina Chtmical AbstruclS as

it appcarswccklyisofpracticallynou,eat 111 Citation, in the Cita!ion Ind•~ will appear undtr 1he /tm-

m1mffl uu1hor(reaardlcss of hi, a<:1ual ,tatu,!) and his ini1ial(1), followed by !h< year, tho abbreviationofthejour nal, vol ume noteot each hern,becu«wi1hname,likeSmithand Jone1or withhpaneseau1hon(e,·en,,,itht"·oinitials)duplicationoflen occurs, and the ,.archer may fi nd him lfpursuin1 aciterin

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ofthedttd publications can beob1aintdju11 bycountina the over, say,$ )'Carsisa1oodomen

Thebestwayofexaminin11eachci1i n1publicationis tolook fimat1hereference,andthentnci11Jthereferen~numberin people 'hide'theexperimentallymonvaluab leinformati on

Mllthod1/n Orgtmk:Synt"-&i#

This monthly publicationbytheRoyalSodetyofChemistryi1

a must for the beginning (and advanced) uarch er and researcher Each issue abstract! article, from cur rent jou,nab

by JivirtJ authotS, reference, ,uuctures ofs1anin1 materials, rea1entsandp1oduc1s.aswellas1ummaryofprocedure,.)'ields andnumberofexamples1iven,ino1herv,·ords any1hinaofsyn-Kraphically1cproducedforeconomyandrapidi1yofpublica1ion (when this publicuion ~rn appeartd it appeartd to this 1u1hor tobearacuriousre,emblancetoaprivatelyinuedpre,iou,onc

by a number of11raduate otudentoat a «nainwel!known uni, veuity in the USA!) Each i"ue has indexes of authors pro-ducts, reaction, reagem1 and reactant< and a1,o a lisi of currently iuucd reviews, book, and conference proceedin11 Altogetherthi1isapublicationwhoseinue1canand1houldbe routinely taken home ove,ni£ht for ri1orou1 and systematic study

HIN TS ON HOW TO SCAN A JOU RNAL

Sofarwehavedweltonthep1oblemofhowto1e11otheri£ht referenceand}ournal Nowafewword,onhov,·1oreadjour-nal,, assurnin1 it is oonerete information in which you ore alternati ve to readirtJ each journal as ii comes in Thi• i,

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abmac1: a caiualreferencc, lchancercmarkor a for1uirous

experimental observation lfow<'>'er, minty spu kina thi, i,

physically imp0ssible Whal one can ,usgc,1 i, some ,peed· the researcher to spo! !he 'hor>e' of fac!I, resul11 and c,posi1ioo andju,1rncarionandpearlso fwisdom 1flCl'thcfact

In 1he fo llowina rexl, most joumal,are referred 10 by their Chrmica/ Absm,c1sabbreviationsforbrcvl1y Wit h Communications (Tn rahrdron Lm., Chrm Commun • Synth Commun., Anatw Chtm fn t Ed Ent/ and the b.ack

p;im of J Am Chm, Soc and J Org Chr m ) scannin111he

liS1ofcontenui,u1uallyenouit,robrinaalltheimp0rtan1fam

to one ', Htcntion; foll details will usually be absent Perhaps oncmorcthinashouldbcche<,ked,tl>ough-footnotcs,whichi, whe,e, u already pointed ou1 much important information m1y bchidden,lobc'pulledou1ofthehllt'whcnthcql>CStion ofp,ioritycserarises!

Full papen necd a differcntapp,oach Probably you will turn 6m101hrucdcsomlcntirelytoorianicchemi1try: J Ort Chtm Tttrahtdron, Synthrsis, I Med Chtm., J Ht terocyc/ Cht m., J Chr m Soc Ptrkin Tra11J Annalen, and the tel·

evant separate pan1 of Bui/ Soc Chim Fr and A~la Chtm

&and Other journals (He/v Chim Act<l, Cht m Ber 81,1/ Cht m Soc /pn.)have an oraanic 1cetion in 1heConten1S liu

but not in !he journal inelf A thi rd 1roup (notably J Am

Cht m.Soc.)makenoattempttohelpthcruderby 1ny subdivi· 1ion,perhapsin1he(forlom)hopeof11<11ln11 1cro11theidca that ' Chcmi11ry is One'

WithrullpapeHitwillnotdoto"lyon1he1irlcofthepaper oron lhcauthor list when maki n1:achoiccon what to read Any"allynovclfindin11wil1n1ostprobablyh1'eb« npubli1he<I oopurincsmaycont 1inde1ailsontheprepara1ionof animp0,-tant tl·dicarbonyJ imenncdia", one on the m«:hani,m of the

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h.owtoopena,terkall)·hinderedepoxidebyanorp.nocopper you ;r you decide from th.e outKt th.al purine,, Clai1en-type reunngememi and 1u11ars have no1hin11 to do with your own lineofwork;andofcourKitwill~uallybeLosttoyouifyou rely on a Keyword Index

So how do you 'gothroU3h.'ajournal from cover to cove,? Bylooki[l£forthekeyi1ems1ha1will se""e asakindofanchor firstandforemo1tstructuralformulae,reactionflowcharu, and condition,uKd lfeveryauthorv.·ould also11ive these priority ealybeca=ofane,·er-increasi~1endency10li.ccompound,

R ", R"etc.;n • l 2.3.ecc.;thi,isnotalways 1hef11ultofthe author, but that oftheEdito, intentonsa,ingmoney Af!uha,ingfixedtheseitemsinyourmind you will be able 1oplaninyourmind1heKanni"loftheExperiment.al=tion 1ha1hi1work isrtliableandreproduciblewillh.ave1akonequal 'treat' (" th.e solution v.•as neated with ") is ft~uent!y con-venientwhenthcau1horh.asfor11onenenctly howitwasdone oftenco,·er up 1loppi ne5.1are 'exposedto .",'subjectionof ', 'protocol" (lookupthercalmcanina!), •a11edo,·erni1ht',

"General direc1ion& as described in Part X' may h.idc the fact that they do not work in Pan XI Apar1 from th.is General OirectionsandMclhodsof1encomainvaluableinformationon venu and rca11entsth.atcaneasllyb<o,etlooked Only after 1h.is sh.ouldyou skim the main text for any1 hin1 that mi1ht be of further value rather than paddi ng and

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at the overall yield and cffom in•olved in roachins the final duct , and 1he effon and upen;,, that goin101hc rugen1 uscd, ra1her1hanonlyatthehiJ h-yicldlaslstcp St1ttmcnu ,uch u 'Further work i, rontinuinJ' or 'ad· ditionalmutuwillbe,eported,ubsequently',onceanimplied threat and ' hcr,off' notice, arenowrarel}' more tha n an off·

r,ro-Perhap, youshouldno1,eadthisuntilafter 1oin1throu&h Chapter 2 If you h•••, and art notentirelyronvinced tha11he futu re, )'OU should stan a card index, to have ii all 'al your fingertips'.There,houldbeacardfo,evcrypossiblctopic,and 1herc1houldbec,-oss-rcferencinacardspoimin1inallfeasible envc!opesorr,apernar,kin,,e1lon,mixcduporusedforo1her purposc1.Therei,non«dtou;,,1hecu!lomary11iffcard,,slip1 plantobeacti'°fora1 lea1c pan of your 'activc'lirei1would paper In cha! way even an index containing l~ 000- 20000i!em, 1till ••ei1h1 leu for trucllina than a ,mall personal computer

"''ithall lhetrimming,

Onecouldmakcsuucstionsoncla11ifica1ion1ucha.sdi,·idin1 1cardindexin101womain1>'1r1&,functionalgroup1ontheone hand,andreactions,mcthodsandconccpuon1heothef.Butin andchan,eor modify ii a,timesonon 1ndc,perienttisac-cumulated Your card index is an CXl<'tl$iOn of your memory ells andshouldremainmictlyyou,privatcdomain.Nevc,e>·er lend yourcardstoanyonod,e

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I Ref,renc,s areii••nwithout authoro,exceptwh eappro priate

2 for journal abbroviatimu the reader should consult the

Cltt m ica/Ab$rracts Sour« lndtx

3 Ref.,encttuegiv,nuniformlyintheorder:•olum•(if any), sn,c (yur); and nm necessarily as in Clttmica/ Almrac/s

where pract icc haschangodover !hey•a•1

Eo mple1

D i:· 'co,H

TH,

,;\,,

Ibuprof en (amiinllammacory dru11)

Information available on rttolution into enantiomers, on a

pos,ibly preparative>eale

IUPAC name: 2·(4'-lsobutylph•nyl)propanoicacid

Chtmiral A bstracts Col/ec:tive Index 1982-1986: nothin& under: propanoic add , 2-(~'.iiobutylphenyl) nor under: propanok acid, 2·phenyl: i.• JUPAC name not usttl h er Consultation of /ndrxGuidr1ndMerc/r; /nder.ahernativ,s found

(a)«· Methyl ·4·(2·methylpropyl)~nieneaceticacid,

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/11du(;uidt:,how,tha1 (a)applie,; hence look«! for

!kHC,.HN'tl<uld, a·m•lb)'l-4-(l·m•th)·lpropyL)

Chemical Absrracts CoJ/tctive Index /981-1986

(R}-or molutionof wi1hchirala,·add (S}- alycoprotcincolumn, 11)4; 2J0570f-

J Liq Chromat 9, 621 (1986) Rt/ I

(;!;}-: resolution of, byaa,chromato· Jra phy, withamphetamin••• d<rivari,ingaseni, 105:202672-J

Chromatagr 378, !25 (1986) Ref l

resolution of, byhiJh-performanu liquidchro ma101raphyof naphthylmcth)'lamidcdcriv., 100;

l26986c-J Chromaro1, 214, 117

(;!;)· and resolutio n of, b)' HPLC : 1114 ;

(R}- l74767m-Am Lab (Fairfitld,

lOS;90672j- J Chromatogr 318

(;!;)-and , epara1ionofdiiutereomeuof, by (R)· untrifuaalTLCofphenylethylamide and(S}- deriv, 104:llOn9r- J

Chroma1a1r JS6, 341 (1986) Ref 6

(Rh chiral separation by HPLCon (SJ-· o, acidalycopro1e;n.t,onded sta!ionary pha«, mobileph ucand

pH effect on, 105; 212524;,-J

Chromato1r 365, 73(1986) Ref 7

(R}-and separation of, frnm racemicmixtu,e

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Ref.8

CMmical Absrracr, CoJ/tttlYr lndu 1977-198/

(:!:)·: resolution ofdiastcre,:,mers of, by liquidchroma1011a9hy following derivatit.11tionwithchiralrca11em,,

94: Sl43Jr-Ana/ Chim Acra, 110,

(R)· and prcpa,a!ionand metabolism of, (S)- : isomericinversioninrclationto,84:

llSS9Sz-J Phurm Sci /iS , ?69

Chrmica/AbJ/ractsColltctiW'lndrx/967- 1971

No ' Bcn,entacrtic acid' in /ndrx-Chanse in nomenclature! Aftercon1ultationof!a1er/ndn Guidrs,pre>iou1name emer11es a1 Hi·dratropleadd, p-lsobutyl Under this name : nothin11on 'resolution', 'separationofiwmers' 'scparationofenantiomcrs";and no li11in11of(R)or(S)

Chrmka/ At>,1rrrc1s Call« rivr lndu 1962- /966

Apinlookedunder: 'Hydra1ropic add, p-lsobutyl'

Only four reference, twoofthemto cthylestcr,norefercnccto'enan· tiomcn· •,e-solution", ' separation',

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nomenclature combination,, and alro

Formu/a/ndt}()

E.stabli1hedHbelonii11Jin Volume 9 Looked at lnde,of 4lh Supplemen tary, Volume:i 9-11 Nol liued und er any or 1he above nomenclaturepo,.j bilities

Thi, example illumatts difficulties cauR<I by nomenclature referrin1 in effen to the same thina: 'resoln.' and •,epn of diastueomers of .' for the racemate and ',epn of from isomer', ' chiulsepn.of'and ·sepn or fromracrmicmixture' for the (R).and(SJ-<namio mers Ref 4 and Ref 11' journal una,·ailable Refs l 2, $, 7, 8 and 9: 1he method, described appearsultable forana\ytica\purpo,eson ly Refs.3and6 appear suitable fo r sep.ara1ion, on 1 ,mall preparative scale

Re f !O: the ab>t ractindicates largescalescpara1io n of dia1tereomerk ,alts and 11ive an example for a rela!cd com pound on a kiloaram scale; hene<c copy of this pa!ent was ordered

Eumple2

CH,-CO-CH - CH - C01Me Method suitable for

la11ie-scale prepara1ion, as a ,ub>tutc for l.4·addition reaction1(henccqucst ionof

£,Z·1eommy probably immaterial)

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tUPAC name: 1'1cthyl 4-o>c0J)<n1-2-enoato

Looked up in Clw>!iul Ab,rr.x:ts lu cst Index under 1-Pentrnok odd , <4-oxo, m<!h)·I a l<r

Compoundobtainodby1Ulphenylation-&•ncralvaluefora,P-unsaturatedy-kC1001tm, panieularone

Ref 3: turn1 out to be Preliminary cation for Ref 2.Allortfcrsto:

Communi-Cht m Btr 96 46S(l96J) Ref, 3a

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