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A New Autocatalytic Thioacetate‐Enal Addition Reaction: A Michael Addition or Not?
Author(s) -
Ilyashenko Gennadiy,
Whiting Andrew,
Wright Allen
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000391
Subject(s) - chemistry , michael reaction , autocatalysis , hemiacetal , addition reaction , reaction calorimeter , organic chemistry , calorimetry , catalysis , physics , thermodynamics
Abstract Rather than proceeding through a Michael‐type or 1,4‐addition, thioacetic acid adds across unsaturated aldehydes in an autocatalytic manner and involving a double exotherm, as demonstrated by both adiabatic and reaction calorimetry. NMR studies show that an intermediate acylthio‐hemiacetal is involved and that the product continues to react competitively with thioacetic acid.