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A new autocatalytic thioacetate-enal addition reaction: A Michael addition or not?

Lookup NU author(s): Professor Allen Wright

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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 acyl-thio-hemiacetal is involved and that the product continues to react competitively with thioacetic acid. © 2010 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.

Publication metadata

Author(s): Ilyashenko G, Whiting A, Wright A

Publication type: Article

Publication status: Published

Journal: Advanced Synthesis & Catalysis

Year: 2010

Volume: 352

Issue: 11-12

Pages: 1818-1825

Print publication date: 16/08/2010

ISSN (print): 1615-4150

ISSN (electronic): 1615-4169

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: http://dx.doi.org/10.1002/adsc.201000391

DOI: 10.1002/adsc.201000391

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