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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles

Author:
Volkova, Yulia A., Averina, Elena B., Vasilenko, Dmitry A., Sedenkova, Kseniya N., Grishin, Yuri K., Bruheim, Per, Kuznetsova, Tamara S., Zefirov, Nikolai S.
Source:
Journal of organic chemistry 2019 v.84 no.6 pp. 3192-3200
ISSN:
1520-6904
Subject:
Lewis acids, aldehydes, alkenes, amides, chemical reactions, chemical structure, esters, ketones, organic chemistry, phosphonates, sulfur, triethylamine
Abstract:
A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed.
Agid:
6326727