Synthesis and dienophilic reactivity of 1,2-difluorovinylphenylsulfone

被引：13

作者：

DeTollenaere, C ^{[1
]}

Ghosez, L ^{[1
]}

机构：

[1] UNIV CATHOLIQUE LOUVAIN, LAB CHIM ORGAN SYNTH, B-1348 LOUVAIN, BELGIUM

来源：

TETRAHEDRON | 1997年 / 53卷 / 50期

关键词：

D O I：

10.1016/S0040-4020(97)10126-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2-Difluorovinylphenylsulfone 5 was conveniently prepared in three steps from chlorotrifluoroethylene. Both E and Z isomers of 5 gave excellent yields of [4+2] cycloadducts with cyclopentadiene. The E isomer reacted with high kinetic exo selectivity. 1,2-Difluorovinylphenylsulfone 5 did not give cycloadducts with highly polar and reactive dienes. Only complex mixtures were obtained. This was assigned to competitive pathways resulting from addition-elimination sequences. Products resulting from such an addition-elimination sequence were obtained from representative nucleophilic reagents. (C) 1997 Elsevier Science Ltd.

引用

页码：17127 / 17138

页数：12

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