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

Authors
YOSHIMATSU M NAITO M KAWAHIGASHI M SHIMIZU H KATAOKA T
Citation
M. Yoshimatsu et al., MEYER-SCHUSTER REARRANGEMENT OF GAMMA-SULFUR-SUBSTITUTED PROPARGYL ALCOHOLS - A CONVENIENT SYNTHESIS OF ALPHA,BETA-UNSATURATED THIOESTERS, Journal of organic chemistry, 60(15), 1995, pp. 4798-4802
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
15
Year of publication
1995
Pages
4798 - 4802
Database
ISI
SICI code
0022-3263(1995)60:15<4798:MROGPA>2.0.ZU;2-N
Abstract
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 reac tions of 3,3-dibutyl-1 -(phenylthio)propargyl alcohol (1k) and 1-(phen ylthio)ethynyl- 1-cyclo alkanols 1l-n with PPSE gave the enyne sulfide s 2k-n exclusively.