Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 3-Nitroisoxazoles

…, YK Grishin, P Bruheim, TS Kuznetsova…

文献索引：Volkova, Yulia A.; Averina, Elena B.; Grishin, Yuri K.; Bruheim, Per; Kuznetsova, Tamara S.; Zefirov, Nikolai S. Journal of Organic Chemistry, 2010 , vol. 75, # 9 p. 3047 - 3052

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被引用次数: 16

摘要

Novel reaction of tetranitromethane (TNM) with electrophilic alkenes in the presence of triethylamine yielding substituted 3-nitroisoxazoles was found and studied. Triethylamine increases the reactivity of TNM toward electrophilic alkenes promoting their heterocyclization, and the reactions proceed in an unusual way. A variety of α, β-unsaturated aldehydes, ketones, esters, amides, phosphonates, and nitro and sulfur compounds was ...