TRIMETHYL BORATE INDUCED THERMAL CYCLOAROMATIZATION OF -1-(PROP-2-YNYL)-3,3-BIS(ALKYLTHIO)-2-PROPEN-1-OLS THROUGH ACETYLENIC OXY-COPE REARRANGEMENT

Authors
GUPTA AK SAMAL SK ILA H JUNJAPPA H
Citation
Ak. Gupta et al., TRIMETHYL BORATE INDUCED THERMAL CYCLOAROMATIZATION OF -1-(PROP-2-YNYL)-3,3-BIS(ALKYLTHIO)-2-PROPEN-1-OLS THROUGH ACETYLENIC OXY-COPE REARRANGEMENT, Tetrahedron letters, 37(16), 1996, pp. 2817-2820
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
16
Year of publication
1996
Pages
2817 - 2820
Database
ISI
SICI code
0040-4039(1996)37:16<2817:TBITCO>2.0.ZU;2-Y
Abstract
The carbinol acetals 2a-h obtained by 1,2-addition of propargylmagnesi um bromide to acyclic alpha-oxoketene dithioacetals 1a-h undergo cyclo aromatization in the presence of trimethyl borate/methanol to give 2,5 -bis(alkylthio)biphenyls 4a-h through acetylenic oxy-Cope rearrangemen t and an unprecedented 1,4-alkylthio shift in the resulting allenic in termediate. Copyright (C) 1996 Published by Elsevier Science Ltd