Title of article
Heterocyclization of electrophilic alkenes with tetranitromethane revisited: regiochemistry and the mechanism of nitroisoxazole formation
Author/Authors
Averina، نويسنده , , Elena B. and Samoilichenko، نويسنده , , Yuri V. and Volkova، نويسنده , , Yulia A. and Grishin، نويسنده , , Yuri K. and Rybakov، نويسنده , , Victor B. and Kutateladze، نويسنده , , Andrei G. and Elyashberg، نويسنده , , Mikhail E. and Kuznetsova، نويسنده , , Tamara S. and Zefirov، نويسنده , , Nikolai S.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2012
Pages
4
From page
1472
To page
1475
Abstract
Revised regiochemistry for the heterocyclization of electrophilic alkenes with tetranitromethane (TNM) in the presence of triethylamine, providing rapid access to nitroisoxazoles, is reported. The formation of 5-nitroisoxazoles previously incorrectly assigned as 3-nitro regioisomers, has now been established unambiguously by X-ray crystallography. Empirical computations with ACD/CNMR Predictor, based both on hierarchical ordering of spherical environments (HOSE) and an algorithm of artificial neural networks (ANN), and also Density Functional Theory computations of the 13C NMR chemical shifts for the 3- versus 5-nitroisoxazoles are shown to consistently match the spectra of the experimentally observed 5-regioisomers.
Keywords
tetranitromethane , Electrophilic alkenes , Nitroisoxazoles , X-ray crystallography , 13C NMR shift calculations
Journal title
Tetrahedron Letters
Serial Year
2012
Journal title
Tetrahedron Letters
Record number
1880290
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