Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles
Volkova, Yulia A.; Averina, Elena B.; Vasilenko, Dmitry A; Sedenkova, Kseniya N; Grishin, Yuri K.; Bruheim, Per; Kuznetsova, Tamara S.; Zefirov, Nikolai S.
Peer reviewed, Journal article
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https://hdl.handle.net/11250/2825762Utgivelsesdato
2019Metadata
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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.