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.
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页码：4798 / 4802
页数：5
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