Ethenesulfonyl Fluoride: The Most Perfect Michael Acceptor Ever Found?

• Published in: Angewandte Chemie International Edition Vol. 55; no. 41; pp. 12664 - 12667
• Main Authors: Chen, Quan, Mayer, Peter, Mayr, Herbert
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 04.10.2016; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Aromatic compounds; Chemistry; Chemistry, Multidisciplinary; electrophilic aromatic substitution; electrophilicity; Fluorides; linear free-energy relationships; Nucleophiles; Photometry; Physical Sciences; Pyridinium; Pyrroles; Reaction kinetics; Science & Technology; ylides; ylides; SULFUR YLIDES; SCOPE; CYCLOPROPANATION; COMBINATIONS; reaction kinetics; CHEMISTRY; NUCLEOPHILIC REACTIVITIES; ELECTROPHILICITIES; electrophilic aromatic substitution; POLAR ORGANIC-REACTIVITY; electrophilicity; linear free-energy relationships

The kinetics of the reactions of ethenesulfonyl fluoride (ESF) with sulfonium and pyridinium ylides were measured photometrically to determine the electrophilicity parameter of ESF according to the correlation lg k20 °C=sN(N+E). With E=−12.09, ESF is among the strongest Michael acceptors in our comp...