SYNTHETIC APPLICATION OF METHYL(PHENYLTHIO)KETENE - SYNTHESIS OF VICINAL-SUBSTITUTED CYCLOPENTENE DERIVATIVES

被引：48

作者：

ISHIDA, M ^{[1
]}

MINAMI, T ^{[1
]}

AGAWA, T ^{[1
]}

机构：

[1] OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA 565,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 13期

关键词：

D O I：

10.1021/jo01327a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl (phenylthio) ketene (1) reacts with olefins to yield-erodo-(phenylthio)cyclobutanones 3, which are converted into a-methylenecyclobutanones 5. On the other hand, the reaction of the ketene 1 with mines gives a mixture of cis-and irans-a-(phenylthio)azetidin-2-ones (7 and 8). a-Methyleneazetidin-2-one 10a was obtained similarly from cs-a-(phenylthio)azetidin-2-one 7a. The reaction of the cyclopentadiene adduct, 7-methyl-7-(phenylthio) bicyclo[3.2.0]-2-hepten-6-one (3a), with various nucleophiles was investigated. The synthetic evaluation and the stereochemistry of the products are discussed. © 1979, American Chemical Society. All rights reserved.

引用

页码：2067 / 2073

页数：7