Conformational transformations and autooxidation of 5-bromo-2-(2-methylpropyl)-5-nitro-1,3,2-dioxaborinane


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Abstract

Conformational study of 5-bromo-2-(2-methylpropyl)-5-nitro-1,3,2-dioxaborinane at the DFT PBE/3ξ level of theory revealed the only sofa–sofa interconversion pathway through a transition state corresponding to 2,5-twist conformer. The barrier to internal rotation of the axial nitro group is several times higher than that for the equatorial nitro group. According to the 1H, 13C, and 11B NMR, IR, and X-ray diffraction data, the main autooxidation products of 5-bromo-2-(2-methylpropyl)-5-nitro-1,3,2-dioxaborinane are 2-bromo-2-nitropropane-1,3-diol and boric acid.

About the authors

O. Yu. Valiakhmetova

Ufa State Petroleum Technological University

Email: kuzmaggy@mail.ru
Russian Federation, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062

T. V. Tyumkina

Institute of Petrochemistry and Catalysis

Email: kuzmaggy@mail.ru
Russian Federation, pr. Oktyabrya 141, Ufa, Bashkortostan, 450075

E. S. Meshcheryakova

Institute of Petrochemistry and Catalysis

Email: kuzmaggy@mail.ru
Russian Federation, pr. Oktyabrya 141, Ufa, Bashkortostan, 450075

L. M. Khalilov

Institute of Petrochemistry and Catalysis

Email: kuzmaggy@mail.ru
Russian Federation, pr. Oktyabrya 141, Ufa, Bashkortostan, 450075

V. V. Kuznetsov

Ufa State Petroleum Technological University; Ufa State Aviation Technical University

Author for correspondence.
Email: kuzmaggy@mail.ru
Russian Federation, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062; ul. K. Marksa 12, Ufa, Bashkortostan, 450008

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