Trimethyl borate induced thermal cycloaromatization of 1-aryl-1-(prop-2-ynyl)-3,3-bis(alkylthio)-2-propen-1-ols through acetylenic oxy-cope rearrangement

Gupta, Arun K. ; Samal, Samir K. ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1996) Trimethyl borate induced thermal cycloaromatization of 1-aryl-1-(prop-2-ynyl)-3,3-bis(alkylthio)-2-propen-1-ols through acetylenic oxy-cope rearrangement Tetrahedron Letters, 37 (16). pp. 2817-2820. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4039(96)00395-4

Abstract

The carbinol acetals 2a-h obtained by 1,2-addition of propargylmagnesium bromide to acyclic α-oxoketene dithioacetals 1a-h undergo cycloaromatization in the presence of trimethyl borate/methanol to give 2,5-bis(alkylthio)biphenyls 4a-henic oxy-Cope rearrangement and an unprecedented 1,4-alkylthio shift in the resulting allenic intermediate.

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