Heterocyclization of electrophilic alkenes with tetranitromethane revisited: regiochemistry and the mechanism of nitroisoxazole formation |
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| Authors: | Elena B Averina Yuri V Samoilichenko Yulia A Volkova Yuri K Grishin Victor B Rybakov Andrei G Kutateladze Mikhail E Elyashberg Tamara S Kuznetsova Nikolai S Zefirov |
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| Institution: | 1. Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow 119992, Russia;2. IPhaC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region 142432, Russia;3. Department of Chemistry and Biochemistry, University of Denver, Denver, CO 80208, USA;4. Advanced Chemistry Development, Moscow Department, 6 Akademik Bakulev Street, Moscow 117513, Russia |
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| 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. |
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