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Reactions of substituted (methylthio)benzylidene Meldrum's acids with secondary alicyclic amines in aqueous DMSO. Evidence for rate-limiting proton transfer

Reactions of substituted (methylthio)benzylidene Meldrum's acids with secondary alicyclic amines in aqueous DMSO. Evidence for rate-limiting proton transfer

Authors :
Bernasconi, Claude F.
Ali, Mahammad
Nguyen, Kelly
Ruddat, Viola
Rappoport, Zvi
Source :
Journal of Organic Chemistry. Dec 24, 2004, Vol. 69 Issue 26, p9248, 7 p.
Publication Year :
2004

Abstract

The replacement of the methylthio group of substituted methylthiobenzylidene Meldrum's acids (2-SMe-Z) by secondary alicyclic amines occurs by a three-step mechanism. A detailed structure-reactivity analysis indicates that for the reaction with piperazine, 1-(2-hydroxythyl)- piperazine, and morpholine it is deprotonation of T(sub A)(super plus or minus) to products is rate limiting.

Details

Language :
English
ISSN :
00223263
Volume :
69
Issue :
26
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.127675498