1224594-11-9Relevant articles and documents
RETRACTED ARTICLE: Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine.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.
, p. 3192 - 3200 (2019/03/20)
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.
