Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 3-Nitroisoxazoles
The Journal of Organic Chemistry2010Vol. 75(9), pp. 3047–3052
Citations Over Time
Yulia A. Volkova, Elena B. Averina, Yuri K. Grishin, Per Bruheim, Tamara S. Kuznetsova, N. S. Zefirov
Abstract
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 alpha,beta-unsaturated aldehydes, ketones, esters, amides, phosphonates, and nitro and sulfur compounds was involved in the heterocyclization reaction, and a wide range of functionalized 3-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic aspects are discussed.
Related Papers
- → Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles(2019)24 cited
- → Ring opening of aziridines with tetranitromethane in the presence of triethylamine. Efficient synthesis of β-tosylamino nitrates(2010)12 cited
- → A simple nitration of electrophilic alkenes with tetranitromethane in the presence of triethylamine. Synthesis of functionalized β-nitroalkenes(2011)8 cited
- → Photochemical Nitration by Tetranitromethane. Part XLII. Photolysis of Some 4-Methoxystyrene Derivatives with Tetranitromethane.(1998)2 cited
- → ChemInform Abstract: Ring Opening of Aziridines with Tetranitromethane in the Presence of Triethylamine. Efficient Synthesis of β‐Tosylamino Nitrates.(2010)