The Journal of organic chemistry

Cooperative N-heterocyclic carbene/Brønsted acid catalysis for the tail-to-tail (co) dimerization of methacrylonitrile

T Kato, S Matsuoka, M Suzuki

Index: Kato, Terumasa; Ota, Yoshiya; Matsuoka, Shin-Ichi; Takagi, Koji; Suzuki, Masato Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8739 - 8747

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Citation Number: 22

Abstract

The first tail-to-tail dimerization of methacrylonitrile (MAN) has been realized by the cooperative use of N-heterocyclic carbene (NHC) and Brønsted acid catalysts, producing 2, 5-dimethylhex-2-enedinitrile with the E/Z ratio of 24: 76. Although the NHC alone was not effective for the catalysis, the addition of alcohols resulted in the significant increase of the dimer yield up to 82% in the presence of 5 mol% NHC. Detailed experimental studies ...