INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFUR-SUBSTITUTED DIENES VIA 3-SULFOLENES

被引：45

作者：

CHOU, SSP

WEY, SJ

机构：

[1] Department of Chemistry, Fu Jen University, Taipei

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 04期

关键词：

D O I：

10.1021/jo00291a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfur-substituted dienes containing an unsaturated alkyl chain were readily prepared from 3-sulfolenes. The intramolecular Diels-Alder (IMDA) reaction of these derivatives was studied for the first time. A sulfonyl group on the diene was found to facilitate the IMDA reaction. Hexahydroindenes were produced in good yield and with high stereoselectivity. Octahydronaphthalenes were also obtained, but the stereoselectivity was low and the IMDA reaction was more sensitive to steric hindrance. © 1990, American Chemical Society. All rights reserved.

引用

页码：1270 / 1274

页数：5

共 39 条

[11] THE DIELS-ALDER REACTION OF DIENES DERIVED FROM SUBSTITUTED 3-(PHENYL-THIO)-3-SULFOLENES
CHOU, SSP
LIOU, SY
TSAI, CY
[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1988, 35 (05) : 379 - 386
[12] COMPARISON OF THE EFFECTS OF SULFENYL, SULFINYL, AND SULFONYL SUBSTITUENTS ON DIENE REACTIVITY AND REGIOSELECTIVITY IN THE DIELS-ALDER REACTION
CHOU, SSP
SUN, DJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (17) : 1176 - 1177
[13] SELECTIVE SYNTHESIS OF 1-ALKYL-2-(PHENYLSULFONYL)-1,3-BUTADIENES
CHOU, SSP
TSAI, CY
SUN, CM
[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1989, 36 (02) : 149 - 152
[14] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED 2-(PHENYLTHIO)-1,3-BUTADIENES
CHOU, SSP
LIOU, SY
TSAI, CY
WANG, AJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) : 4468 - 4471
[15] CONVENIENT SYNTHESES OF HYDROINDANS AND HYDRONAPHTHALENES
CHOU, TS
TSO, HH
CHANG, LJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (04) : 236 - 237
[16] SELECTIVE CROSS DIELS-ALDER REACTIONS OF 2-(PHENYLSULFONYL) 1,3-DIENES
CHOU, TS
HUNG, SC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) : 3020 - 3027
[17] PREPARATION OF 2,3-DIHETERO-SUBSTITUTED 1,3-DIENES FROM BROMINATED 2-SULFOLENES
CHOU, TS
LEE, SJ
PENG, ML
SUN, DJ
CHOU, SSP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) : 3027 - 3031
[18] Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
[19] COMPLETE REGIOSPECIFICITY AND STEREOSPECIFICITY IN THE LEWIS ACID-CATALYZED DIELS-ALDER REACTIONS OF (Z)-2-METHOXY-1-(PHENYLTHIO)-1,3-BUTADIENES - CONVERSION OF THE CS-CONFIGURATION OF AN ADDUCT TO THE CC-CONFIGURATION AT THE ALLYLIC POSITION BY A [2,3] SIGMATROPIC REARRANGEMENT
COHEN, T
KOSARYCH, Z
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) : 4005 - 4008
[20] INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFONYL-SUBSTITUTED TRIENES
CRAIG, D
FISCHER, DA
KEMAL, O
PLESSNER, T
[J]. TETRAHEDRON LETTERS, 1988, 29 (48) : 6369 - 6372

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