[3+2]-ANNULATION USING ALLYLIDENE(TRIPHENYL)PHOSPHORANES - A ONE-STEP SYNTHESIS OF CYCLOPENTADIENES

被引：31

作者：

HATANAKA, M ^{[1
]}

HIMEDA, Y ^{[1
]}

UEDA, I ^{[1
]}

机构：

[1] NATL INST MAT & CHEM RES,DEPT MOLEC ENGN,TSUKUBA,IBARAKI 305,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 19期

关键词：

D O I：

10.1039/p19930002269

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient method for the synthesis of substituted cyclopentadienes has been developed using allylidene(triphenyl)phosphoranes. (3-Ethoxycarbonyl-2-substituted-2-propenylidene)triphenylphosphoranes 1 reacted with alpha-halogenoketones under very mild reaction conditions to undergo a [3 + 2]-annulation leading to the regioselective formation of tri- or tetra-substituted cyclopentadienes in good to excellent yields. Allylidenephosphoranes 1 also reacted with S-ethyl bromoethanethioate to yield 4-ethylthiocyclopentadienes, which was readily converted into a cyclopentenone.

引用

页码：2269 / 2274

页数：6

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