BIS(TERT-BUTYLSULFONYL)ACETYLENE AS A GENERAL SYNTHETIC EQUIVALENT OF ALKYNES IN DIELS-ALDER CHEMISTRY .1. HIGHLY SELECTIVE REDUCTION AND ALKYLATING MONODESULFONYLATION OF Z-1,2-BIS(TERT-BUTYLSULFONYL)ETHENES

被引：9

作者：

BELLOCH, J ^{[1
]}

VIRGILI, M ^{[1
]}

MOYANO, A ^{[1
]}

PERICAS, MA ^{[1
]}

RIERA, A ^{[1
]}

机构：

[1] UNIV BARCELONA,DEPT QUIM ORGAN,MARTI & FRANQUES 1-11,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 35期

关键词：

D O I：

10.1016/0040-4039(91)80044-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic (Z)-1,2-Bis(tert-butylsulfonyl)ethenes arising from Diels-Alder reactions of bis(tert-butylsulfonyl)acetylene are efficiently reduced to monosulfones by samarium(II) iodide and alkylatively monodesulfonylated by organolithium compounds.

引用

页码：4579 / 4582

页数：4

共 15 条

[1] 1,2-BIS(PHENYLSULFONYL)ALKENES AS VERSATILE GROUPS IN ORGANIC-SYNTHESIS - THE PREPARATION OF ALKYL-SUBSTITUTED AND ARYL-SUBSTITUTED NORBORNADIENES VIA THE DIELS-ALDER CYCLOADDITION-GRIGNARD REACTION-DESULFONYLATION SEQUENCE
AZZENA, U
COSSU, S
DELUCCHI, O
MELLONI, G
[J]. TETRAHEDRON LETTERS, 1989, 30 (14) : 1845 - 1848
[2] SYNTHESIS USING SULFONES .24. STEREOSELECTIVE SYNTHESIS OF OLEFINS BY HYDROGENOLYSIS OF VINYLSULFONES
BREMNER, J
JULIA, M
LAUNAY, M
STACINO, JP
[J]. TETRAHEDRON LETTERS, 1982, 23 (32) : 3265 - 3266
[3] ETHYNYL PARA-TOLYL SULFONE AS AN ACETYLENE EQUIVALENT IN DIELS-ALDER REACTIONS
DAVIS, AP
WHITHAM, GH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (13) : 639 - 640
[4] DELUCCHI O, 1984, TETRAHEDRON, V40, P2585
[5] THE ROLE OF SULFUR FUNCTIONALITIES IN ACTIVATING AND DIRECTING OLEFINS IN CYCLO-ADDITION REACTIONS
DELUCCHI, O
PASQUATO, L
[J]. TETRAHEDRON, 1988, 44 (22) : 6755 - 6794
[6] REACTIVITY OF PHENYL(TOLYLSULFONYL)ACETYLENE TOWARDS DIENES AND HOMO-DIENES - CYCLO-ADDITIONS VERSUS FRAGMENTATION-ADDITION REACTIONS
DELUCCHI, O
LICINI, G
PASQUATO, L
SENTA, M
[J]. TETRAHEDRON LETTERS, 1988, 29 (07) : 831 - 834
[7] MIXED COUPLING BETWEEN VINYLIC SULFONES AND GRIGNARD-REAGENTS IN THE PRESENCE OF SALTS OF TRANSITION-METALS - STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED OLEFINS
FABRE, JL
JULIA, M
VERPEAUX, JN
[J]. TETRAHEDRON LETTERS, 1982, 23 (24) : 2469 - 2472
[8] A SIMPLE AND VERSATILE ACETYLENE EQUIVALENT IN DIELS-ALDER REACTIONS
KUMAR, PR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (08) : 509 - 510
[9] REDUCTIVE DESULFONYLATION OF PHENYL SULFONES BY SAMARIUM(II) IODIDE-HEXAMETHYLPHOSPHORIC TRIAMIDE
KUNZER, H
STAHNKE, M
SAUER, G
WIECHERT, R
[J]. TETRAHEDRON LETTERS, 1991, 32 (17) : 1949 - 1952
[10] REGIOSELECTIVE PREPARATION OF CYCLOHEXADIENES OR AROMATIC NITRO-COMPOUNDS BY DIELS-ALDER REACTIONS OF BETA-SULFONYLNITROOLEFINS OR BETA-SULFINYLNITROETHYLENE
ONO, N
KAMIMURA, A
KAJI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) : 251 - 258

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