INTERMEDIATES FOR THE SYNTHESIS OF LINEAR-CHAINS OF 1,2/4,5-FUSED CYCLOHEXA-1,4-DIENE RINGS AND BELTENES BY REPEATED DIELS-ALDER REACTIONS

被引:17
作者
ALDER, RW
ALLEN, PR
EDWARDS, LS
FRAY, GI
FULLER, KE
GORE, PM
HEXT, NM
PERRY, MH
THOMAS, AR
TURNER, KS
机构
[1] School of Chemistry, University of Bristol
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 21期
关键词
D O I
10.1039/p19940003071
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthetic strategy for the preparation of chains of 1,2:4,5-fused cyclohexa-1,4-diene rings, both linear and cyclic (beltenes), based on the repetitive Diels-Alder cycloaddition of p-benzoquinone with a tetramethylene- ethane synthon (3,4-dimethylenetetrahydrothiophene 1,1-dioxide) is described. This route has been developed to yield 5,11-dihydroxy-4,6,7,9,10,12-hexahydro-1H,3H-anthracene-[2,3-c:6,7-c']dithiophene 2,2,8,8-tetraoxide 16, a potential precursor of a tricyclic doubly-exocyclic diene, and 7,10-bis(tert-butyldimethylsilyloxy)-1,4,5,6,11,12-hexahydronaphthacene-1,4-dione 22, a potential precursor for the double dienophile 5,6,11,12-tetrahydronaphthacene-1,4,7,10-diquinone. but the generation of these Diels-Alder components and their combination to form a [9]-beltene derivative has not been accomplished. The synthesis of linear derivatives has proceeded as far as a protected heptacyclic derivative. 7,16-diacetoxy-1,4,10,13-tetrakis(tert-butyldimethylsilyloxy)-5,6,8,9,14,15,17,18-octahydroheptacene 25. The H-1 NMR spectrum of this compound is unexpectedly temperature dependent.
引用
收藏
页码:3071 / 3077
页数:7
相关论文
共 44 条
  • [1] FORCE-FIELD CALCULATIONS ON MOLECULAR BELTS BUILT FROM CYCLOHEXA-1,4-DIENE RINGS
    ALDER, RW
    SESSIONS, RB
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (11): : 1849 - 1854
  • [2] ELECTRONIC-STRUCTURE AND NEAR-INFRARED SPECTRA OF DIQUINONE ANION RADICALS
    ALMLOF, JE
    FEYEREISEN, MW
    JOZEFIAK, TH
    MILLER, LL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) : 1206 - 1214
  • [3] COLUMNAR HOMOCONJUGATION
    ANGUS, RO
    JOHNSON, RP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) : 314 - 317
  • [4] ANGUS RO, 1985, THESIS IOWA STAT U A
  • [5] DIELS-ALDER REACTION OF P-BENZOQUINONES
    ANSELL, MF
    NASH, BW
    WILSON, DA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1963, (MAY): : 3012 - &
  • [6] TRINACRENE - A PRODUCT OF STRUCTURE-DIRECTED SYNTHESIS
    ASHTON, PR
    ISAACS, NS
    KOHNKE, FH
    DALCONTRES, GS
    STODDART, JF
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (09): : 1261 - 1263
  • [7] TOWARDS THE MAKING OF [12]COLLARENE
    ASHTON, PR
    ISAACS, NS
    KOHNKE, FH
    SLAWIN, AMZ
    SPENCER, CM
    STODDART, JF
    WILLIAMS, DJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (07): : 966 - 969
  • [8] MOLECULAR BELTS .2. SUBSTRATE-DIRECTED SYNTHESES OF BELT-TYPE AND CAGE-TYPE STRUCTURES
    ASHTON, PR
    GIRRESER, U
    GIUFFRIDA, D
    KOHNKE, FH
    MATHIAS, JP
    RAYMO, FM
    SLAWIN, AMZ
    STODDART, JF
    WILLIAMS, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) : 5422 - 5429
  • [9] MOLECULAR LEGO .1. SUBSTRATE-DIRECTED SYNTHESIS VIA STEREOREGULAR DIELS-ALDER OLIGOMERIZATIONS
    ASHTON, PR
    BROWN, GR
    ISAACS, NS
    GIUFFRIDA, D
    KOHNKE, FH
    MATHIAS, JP
    SLAWIN, AMZ
    SMITH, DR
    STODDART, JF
    WILLIAMS, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) : 6330 - 6353
  • [10] STEREOREGULAR OLIGOMERIZATION BY REPETITIVE DIELS-ALDER REACTIONS
    ASHTON, PR
    ISAACS, NS
    KOHNKE, FH
    MATHIAS, JP
    STODDART, JF
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (09): : 1258 - 1261