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Relative stability of 5-methyl- and 3,5-dimethyltetrahydro-1,3-oxazine conformers

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Abstract

According to HF and DFT quantum chemical calculations and 1H NMR data, the chair–chair conformational equilibrium of 5-methyltetrahydro-1,3-oxazine shifts toward the conformer with equatorial orientation of the methyl group on C5 and axial orientation of the NH proton. 3,5-Dimethyltetrahydro-1,3-oxazine exists preferentially as chair conformer with equatorial orientation of the 5-methyl group; orientation of the N-methyl group almost does not affect the conformational equilibrium.

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Authors and Affiliations

  1. Ufa State Aviation Technical University, ul. K. Marksa 12, Ufa, 450008, Bashkortostan, Russia

    V. V. Kuznetsov

  2. Ufa State Petroleum Technological University, ul. Kosmonavtov 1, Ufa, 450000, Bashkortostan, Russia

    V. V. Kuznetsov

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  1. V. V. Kuznetsov
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Correspondence to V. V. Kuznetsov.

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Original Russian Text © V.V. Kuznetsov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 3, pp. 429–433.

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Kuznetsov, V.V. Relative stability of 5-methyl- and 3,5-dimethyltetrahydro-1,3-oxazine conformers. Russ J Org Chem 52, 409–413 (2016). https://doi.org/10.1134/S1070428016030192

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  • DOI: https://doi.org/10.1134/S1070428016030192

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