1
CHEhlISTlZY AND INDUSTRY 5111y 6, 1933 390 Lastly conic tltc clinngcs comprised undcr the hcndings of isoincrizntion iind polynicriziition. Tltc work is tltorouglt, conscientious, nnd complctc in tllc innnncr wlticli we Iinvc grown to cspcct of nll tlic AbdcrItiiIdcn tcst-boola ; n good dcnl inorc considcr- ation is givcn to tlic noii-Gcrninn litcrnturc tlinn at onc time used to hc tlic ciisc wit,li Gcrtnnn books. This is esscutiul m~-niluys, when thc one-time Gcrman suprcmncy lins pnssetl, nnd tlic originnl u-orkcr looks \'cry Inrgely to Uritish nnd ilnicricrin litcrnturc for his inspiration. In rclntion to tlic information arnilnblc thc price is relatively tnodcrntc, and thc book will prob:tbly hc found of grcnt itsc in most rcscnrcli laborntorics. HAXDIWCII DER IhoLocisciies r\i~i~I.:I'rsJtE:Tiiot)iSs. IEditcd I J ~ l'rof. E. ~ll~tlcrliiil~lcn. Die Jlctltodcn dcr I>iclt-syntllcSe. By I<. Aldcr. Aht. I, Cltctnisclte Jlcthodcn, l'eil 2, 2. HHlftc, 1.Icft 9 (Schluss). Licfcrung 400. 1'11. 3Oi9--3291. 13crli11 : (Jr1Ji111 S: Schw:ir~cnbcrg, 1933. 13.50 rnt. According to tlic wcll-kno\rn tlicory of Tliiclc, a symmctriciilly constitntcd dicnc of tlic forin C = C - C = C yields 1,4-:1tldition, owing to tlto . posscssion of frce iiflinit,y Iiy cnrlioit ntotns 1 irnd 4, tll1ls : c = c - c' = c + c's - c: =r. c - cs; :\I- t.hongli thcrc nre initiiy cset!ptions to this gcncriilizntion, thc si)cci:il type of 1 ,.l-nddit ion discusscd in tlic prcscnt trcat,isc tnkcs plncc with snch ccrtuinty t riut it Ii:ts IJ~C~IIIC a viilunblc diagnostic adjunct and synt,lictit: principle. Tlic so-ciillcd dicnc syitlicsis ltns ctlictgetl iis n rmlllt of cstcnsivc inrcstigit,ions conductcil by llicls iiid Nrlcr sincc 19%. Thc couiac of crciits in t,Bc dicnc syntliesis niuy be forniulateii in perill tcrnis as fullo\\.s : (u) Cotlipo1tIds contiiiiiing a systcin of conjugutcd double bontls yield 1,4-addit.ion with coinliouncls coiitiiining :in nct,irc ctltylcnc or iicctylctrc linking, tliClCby giving risc to iL pir t l y li yd rogctiii t ctl sis-titcinbcrecl ring-sys t c in ; (6) t lie iictivittiott of tlic ctly'lcnc or ricetylcnc linking is Lrougltt iibout I)y niciins of nil unsnturatcd group (> C = 0, -C 2 N, > C =I C <, und possibly --NO,) situutctl in the a@-pot-:ition. l'hc nut,lior givcs n systcniiitic review (Jf iinport:int siiI,stancc.=, fitlling nndor t liu two ltcntls, wliicli linvc Iiecn found to ~CJllf~rlll to the II l~ove principle, iind priictic:il condit.ions lire also tlisciissctl. Of tlic iiiiiny interesting iipplicut~ions of tlic tlicnc syiitlicsis, it must suliicc to quote n few rcl)rescnt;iti\*e iiiituriil violct ketontr irhioli W:IP isoliitcd hy 'l'ictniinn iiiid Kriigcr in it yield of less tliiin 0.0070/, fruni violct roots. Tlic very coinplicutcd nntl IiiIJorioiis synt,licsis of this kctolic IIY JIcrling iitid IVcld~ stiltids in t1l:irl;cd coiitrast to tlic fucilc two-st;igc tliciio syntliesis froin I,l-dii~ictliyll~i~tcidictic niid crotonic iildcllytla. Etltiully nttriictivc iIttd iinlircssiw itrc tlic syntlicscs of wr- cnniphor (ix., tlic fuitdtiiiicntal cyclic ketone or wliicli cnniphor is the triiuctliyl-ileri\.iitivc), wid, tliroiigh tliis, of c:rniphcnc, from cyclclopciitudicnc iind ucrolciii. Tlic principle of dicnc synthesis upplicn itot only to acyclic u~itl lioniocyclic diencs, I)iit ~ilsi, to Ilctcrocyclic systolns with oxygcn in tlic ritig, sucli as furiIIl iiitrl 1 2 3 4 ~ S ~ I I I ~ I ~ S . il iiotitblc synthesis is tlliit of [i-ir(ilic, tllc couninliu. Addition OCCII~S ;ilso in tltc cnsc 01 nitrogenous rings, but in sucli instnticcs thc r ~ i ~ t i 0 1 1 follows another coursc, wliich it ~voultl talcc too long to discuss in this plricc. It is difficult in n sliort rcvicw to do justicc to llr. Aldcr's ublc siintni:iry and csposition of tltcsc iniportnltt originill rcscnrclics in which he Ims tnlicn so nctivc ir part, hut 1)~';Ititps cttollgli 113s IJCCll sitid to slto\\. tltiit organic clicniists ant1 bioclicrnists dike will derive n~uch profit from :I sttidy of this innity-sidcd t1i:ignostic and syntltctic nictliod. Tlic viiricty of syntlicscs to irlticli it :iffords :ti1 opening is nstonislring, rind tlic cl:iI~oriition of sonic of tlic inolcciiliir 1):ittcriis-piirticitI:irl~ t lie polycyclic ones-proviilc cscrciscs iii ntolccul:tr cltcss srirl)wsing in interest evc~t tlic 1)roIhis of the ~tiiicro- scopic giinic. .Jotis ~~ILII) StJLPIlUR I)ACTE:IIIA. Ijy1). Icliis, 1).sc., 1'1i.T). 1'1). ix $- 261. Lotldolt : I,OII~IIIU~S, Orccn s: CO., 1932. 21s. The bnctcrin which oxidize sulpliur ilntl its conipoIii1ds arc of grciit interest iind iinportiince from both inorplio- Iogicnl itrid pliysiologicnl points of view. Tlic bio- chcinistry of sulpliur osidntion iind t lie suppt~sc"1 photosynthetic ncti ri ty ~mscsscd I y those Imtcricr that contain purple pigniciit offcr fields of rcsciirch which promisc irnportiint adv:tnces in our undcr- standing of the physiology of living inrittcr, while thcsc purplc biictcria displiiy 11 inost interesting cxiiniplc of pliototropisni. Sulphur 1Jnctcriir hirvc trlso it con- sidcrnblc pet icid iinportriticc in soil biictcriology, and in conticsion with wntcr supply. Thcy iniry hnvc u beiiring on tlic cicute prol)lciii of the dccuy of The group conttiins witlcly tlivcrsc ntorpliologicitl types, rind the coiniiion groutit1 posscsscil by tltcni ivould iippcitr to be pliysiologicd. Yct the nutlior dclincs " sulpltitr bitctcriu " :is biictcrju wliicli havc sulphur ~IOIJUICS in tlicir cells, nnd lie cscludes from thc ~iiriin pirt of tlic book iin iniportaiit group for tbc reiisoii that, in their ciisc, tlic sulpliur iicciiniuliitcs outside the cells. This ctppciirs insutlicicnt gruitntl for tlic cxcliision of tliis group, cspeciiilly sincc tlic itutlior says tliat with his truc..ylpliur bncterin " the sulpliur appears to be cxcrcted iintl ositlizctl to srilpli:itc ont- side tlic cell." The group wliiclt he tlius cxcludcs contiiiiis thc orgunisin l'liiob~xillus fhiooxid4~iis, iilthoiigh hc iticludes otltcr spccics of tltc suinc gciius Y'hiobucillus in his clitssilication of the true sulpltur Ixictcriir. d lurgc prt of the Imok tlciils with tltc tnorphologicitl description of known types of sull)liur-corititiuirt~ bnctcrin, but in rnitny citscs tlic descriptions of the orgnnisins urc too incotnplctc to wnrrtitit the creirtioit of spccific niiiiics. The itutlior rightly drirwti irttcntion to tlic opportnnity oflcred IJY sowe of tltc Irtrgc-ccllcd sulphur orgiinisins for thc invcstigirtioti of IJitctcriul cytology iirtd of tho vexcd prol)leiti of ttic iiictliodH of reproduction irrnongst buctcriir. The vuluc of obscrvirtions inutIc in thcse subjects itl ciitircly t1cI)cndcitti on the tcchtiiquc CIU- ploycd, so that the iiiritlcqiiutc description of thiH technique rcitdcrs the vitluc of thc author's coiiclusioits dinicult to ntjscss. Thcrc RI'C interesting scctions ;on the phototropism of tltc coloiirctl buctcriir ~ind upon 6tOrlc.

Handbuch der biologischen arbeitsmethoden. Edited by Prof. E. Abderhalden. Die Methoden der Dien-synthese. By K. Alder. Abt. I, Chemische Methoden, Teil 2, 2. Hälfte, Heft 9 (Schluss)

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Page 1: Handbuch der biologischen arbeitsmethoden. Edited by Prof. E. Abderhalden. Die Methoden der Dien-synthese. By K. Alder. Abt. I, Chemische Methoden, Teil 2, 2. Hälfte, Heft 9 (Schluss)

CHEhlISTlZY AND INDUSTRY 5111y 6 , 1933 390

Lastly conic tltc clinngcs comprised undcr the hcndings of isoincrizntion iind polynicriziition.

Tltc work is tltorouglt, conscientious, nnd complctc in tllc innnncr wlticli we Iinvc grown to cspcct of nll tlic AbdcrItiiIdcn tcst-boola ; n good dcnl inorc considcr- ation is givcn to tlic noii-Gcrninn litcrnturc tlinn at onc time used to hc tlic ciisc wit,li Gcrtnnn books. This is esscutiul m~-niluys, when thc one-time Gcrman suprcmncy lins pnssetl, nnd tlic originnl u-orkcr looks \'cry Inrgely to Uritish nnd ilnicricrin litcrnturc for his inspiration. In rclntion to tlic information arnilnblc thc price is relatively tnodcrntc, and thc book will prob:tbly hc found of grcnt itsc in most rcscnrcli laborntorics.

HAXDIWCII DER IhoLocisciies r\i~i~I.:I'rsJtE:Tiiot)iSs. IEditcd I J ~ l'rof. E. ~ll~tlcrli i i l~lcn. Die Jlctltodcn dcr I>iclt-syntllcSe. By I<. Aldcr. Aht. I, Cltctnisclte Jlcthodcn, l'eil 2, 2. HHlftc, 1.Icft 9 (Schluss). Licfcrung 400. 1'11. 3Oi9--3291. 13crli11 : (Jr1Ji111 S: Schw:ir~cnbcrg, 1933. 13.50 rnt.

According to tlic wcll-kno\rn tlicory of Tliiclc, a symmctriciilly constitntcd dicnc of tlic forin C = C - C = C yields 1,4-:1tldition, owing to tlto

. posscssion of frce iiflinit,y Iiy cnrlioit ntotns 1 irnd 4 , tll1ls : c = c - c' = c + c's - c: =r. c - cs; :\I- t.hongli thcrc nre initiiy cset!ptions to this gcncriilizntion, thc si)cci:il type of 1 ,.l-nddit ion discusscd in tlic prcscnt trcat,isc tnkcs plncc with snch ccrtuinty t r iu t it Ii:ts I J ~ C ~ I I I C a viilunblc diagnostic adjunct and synt,lictit: principle. Tlic so-ciillcd dicnc syitlicsis ltns ctlictgetl iis n rmlllt of cstcnsivc inrcstigit,ions conductcil by llicls i i i d Nrlcr sincc 19%.

Thc couiac of crciits i n t,Bc dicnc syntliesis niuy be forniulateii in p e r i l l tcrnis as fullo\\.s : (u) Cotlipo1tIds contiiiiiing a systcin of conjugutcd double bontls yield 1,4-addit.ion with coinliouncls coiitiiining :in nct,irc ctltylcnc or iicctylctrc linking, tliClCby giving risc to iL

p i r t l y l i yd rogctiii t ctl sis-titcinbcrecl ring-sys t c i n ; (6) t lie iictivittiott of tlic ctly'lcnc or ricetylcnc linking is Lrougltt iibout I)y niciins of nil unsnturatcd group (> C = 0, -C 2 N, > C =I C <, und possibly --NO,) situutctl i n the a@-pot-:ition. l'hc nut,lior givcs n systcniiitic review ( J f iinport:int siiI,stancc.=, fitlling nndor t liu two ltcntls, wliicli linvc Iiecn found to ~ C J l l f ~ r l l l to the I I l~ove principle, iind priictic:il condit.ions lire also tlisciissctl.

Of tlic iiiiiny interesting iipplicut~ions of tlic tlicnc syiitlicsis, it must suliicc to quote n few rcl)rescnt;iti\*e

iiiituriil violct ketontr irhioli W:IP isoliitcd hy 'l'ictniinn iiiid Kriigcr i n it yield of less tliiin 0.0070/, fruni violct roots. Tlic very coinplicutcd n n t l IiiIJorioiis synt,licsis of this kctolic I I Y JIcrling iitid IVcld~ stiltids i n t1l:irl;cd coiitrast to tlic fucilc two-st;igc tliciio syntliesis froin I,l-dii~ictliyll~i~tcidictic n i i d crotonic iildcllytla. Etltiully nttriictivc iIttd iinlircssiw itrc tlic syntlicscs of w r - cnniphor (ix., tlic fuitdtiiiicntal cyclic ketone or wliicli cnniphor is the triiuctliyl-ileri\.iitivc), wid, tliroiigh tliis, of c:rniphcnc, from cyclclopciitudicnc iind ucrolciii.

Tlic principle of dicnc synthesis upplicn itot only to acyclic u~it l lioniocyclic diencs, I)iit ~ilsi, to Ilctcrocyclic systolns with oxygcn in tlic ritig, sucli as furiIIl iiitrl

1 2 3 4

~ S ~ I I I ~ I ~ S . il iiotitblc synthesis is tlliit of [i-ir(ilic, tllc

couninliu. Addition OCCII~S ;ilso i n tltc cnsc 01 nitrogenous rings, but in sucli instnticcs thc r ~ i ~ t i 0 1 1 follows another coursc, wliich it ~voultl talcc too long to discuss i n this plricc.

It is difficult in n sliort rcvicw to do justicc to llr. Aldcr's ublc siintni:iry and csposition of tltcsc iniportnltt originill rcscnrclics i n which he Ims tnlicn so nctivc ir

part, hut 1)~';Ititps cttollgli 113s IJCCll sitid to slto\\. tltiit organic clicniists ant1 bioclicrnists d ike will derive n~uch profit from :I sttidy of this innity-sidcd t1i:ignostic and syntltctic nictliod. Tlic viiricty of syntlicscs t o irlticli it :iffords :ti1 opening is nstonislring, rind tlic cl:iI~oriition of sonic of tlic inolcciiliir 1):ittcriis-piirticitI:irl~ t lie polycyclic ones-proviilc cscrciscs iii ntolccul:tr cltcss srirl)wsing i n interest evc~t tlic 1)roIhis of the ~tiiicro- scopic giinic. .Jotis ~ ~ I L I I )

StJLPIlUR I)ACTE:IIIA. Ijy1). Icliis, 1).sc., 1'1i.T). 1'1). ix $- 261. Lotldolt : I , O I I ~ I I I U ~ S , Orccn s: CO., 1932. 21s.

The bnctcrin which oxidize sulpliur ilntl its conipoIii1ds arc of grciit interest i i n d iinportiince from both inorplio- Iogicnl itrid pliysiologicnl points of view. Tlic bio- chcinistry of sulpliur osidntion iind t lie suppt~sc"1 photosynthetic ncti r i ty ~mscsscd I y those Imtcricr that contain purple pigniciit offcr fields of rcsciirch which promisc irnportiint adv:tnces i n our undcr- standing of the physiology of living inrittcr, while thcsc purplc biictcria displiiy 11 inost interesting cxiiniplc of pliototropisni. Sulphur 1Jnctcriir hirvc trlso it con- sidcrnblc p e t icid iinportriticc i n soil biictcriology, and in conticsion with wntcr supply. Thcy iniry hnvc u beiiring on tlic cicute prol)lciii of the dccuy of

The group conttiins witlcly tlivcrsc ntorpliologicitl types, rind the coiniiion groutit1 posscsscil by tltcni ivould iippcitr to be pliysiologicd. Yct the nutlior dclincs " sulpltitr bitctcriu " :is biictcrju wliicli havc sulphur ~ I O I J U I C S in tlicir cells, nnd lie cscludes from thc ~ i i r i in pi r t of tlic book i i n iniportaiit group for tbc reiisoii that, in their ciisc, tlic sulpliur iicciiniuliitcs outside the cells. This ctppciirs insutlicicnt gruitntl for tlic cxcliision of tliis group, cspeciiilly sincc tlic itutlior says tliat with his truc..ylpliur bncterin " the sulpliur appears to be cxcrcted iintl ositlizctl to srilpli:itc ont- side tlic cell." The group wliiclt he tlius cxcludcs contiiiiis thc orgunisin l'liiob~xillus fhiooxid4~iis, iilthoiigh hc iticludes otltcr spccics of tltc suinc gciius Y'hiobucillus in his clitssilication of the true sulpltur Ixictcriir. d lurgc p r t of the Imok tlciils with tltc tnorphologicitl

description of known types of sull)liur-corititiuirt~ bnctcrin, but in rnitny citscs tlic descriptions of the orgnnisins urc too incotnplctc to wnrrtitit the creirtioit of spccific niiiiics.

The itutlior rightly drirwti irttcntion to tlic opportnnity oflcred IJY sowe of tltc Irtrgc-ccllcd sulphur orgiinisins for thc invcstigirtioti of IJitctcriul cytology iirtd of tho vexcd prol)leiti of ttic iiictliodH of reproduction irrnongst buctcriir. The vuluc of obscrvirtions inutIc in thcse subjects itl ciitircly t1cI)cndcitti on the tcchtiiquc CIU- ploycd, so that the iiiritlcqiiutc description of thiH technique rcitdcrs the vitluc of thc author's coiiclusioits dinicult to ntjscss. Thcrc RI'C interesting scctions ;on the phototropism of tltc coloiirctl buctcriir ~ind upon

6tOrlc.