MEYER-SCHUSTER REARRANGEMENT OF GAMMA-SULFUR-SUBSTITUTED PROPARGYL ALCOHOLS - A CONVENIENT SYNTHESIS OF ALPHA,BETA-UNSATURATED THIOESTERS

被引：35

作者：

YOSHIMATSU, M ^{[1
]}

NAITO, M ^{[1
]}

KAWAHIGASHI, M ^{[1
]}

SHIMIZU, H ^{[1
]}

KATAOKA, T ^{[1
]}

机构：

[1] GIFU PHARMACEUT UNIV,GIFU 502,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 15期

关键词：

D O I：

10.1021/jo00120a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

gamma-Sulfur-substituted propargyl alcohols 1a-e and 1ij reacted with polyphosphoric acid trimethylsilyl ester (PPSE) to give the alpha,beta-unsaturated thioesters 3a-e and 3ij in good yields. However, the reactions of 3,3-dibutyl-1 -(phenylthio)propargyl alcohol (1k) and 1-(phenylthio)ethynyl- 1-cyclo alkanols 1l-n with PPSE gave the enyne sulfides 2k-n exclusively.

引用

页码：4798 / 4802

页数：5

共 11 条

[1]

COUTROT P, 1991, SYNTHESIS-STUTTGART, P23

[2] SYNTHESIS AND REACTIONS OF A STABLE 2-SELENANAPHTHALENE, 1-CYANO-2-METHYL-2-SELENANAPHTHALENE [J].