A New Autocatalytic Thioacetate??Enal Addition Reaction: A Michael Addition or Not?

G Ilyashenko, A Whiting, A Wright

Index: Ilyashenko, Gennadiy; Whiting, Andrew; Wright, Allen Advanced Synthesis and Catalysis, 2010 , vol. 352, # 11-12 p. 1818 - 1825

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Citation Number: 3

Abstract

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.