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Solvent‐free Thia‐Michael Addition Reactions Using 3‐[Bis(alkylthio)methylene]pentane‐2,4‐diones as Efficient and Odorless Thiol Equivalents
Author(s) -
LIN Chun,
ZHAO XiaoLiang,
OUYANG Yan,
YU HaiFeng,
DONG DeWen
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890260
Subject(s) - chemistry , methylene , michael reaction , thiol , pentane , organic chemistry , solvent , conjugate , medicinal chemistry , catalysis , mathematical analysis , mathematics
3‐[Bis(alkylthio)methylene]pentane‐2,4‐diones ( 1a and 1b ) have been investigated as nonthiolic and odorless thiol equivalents for thia‐Michael addition reactions under solvent‐free conditions. Promoted by HCl (aq.), the cleavage of compounds 1 took place, and the in‐situ generated thiols underwent facile conjugate addition to α ? β ‐unsaturated carbonyl compounds 2 affording the corresponding ‐keto sulfides 3 in high yields.