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Heterocumulenes reactions with organometallic reagents: XV. Quantum-chemical investigatiom of skeleton rearrangements of 2-methyl-6-methoxy-3H-azepine originating from valence tautomerism

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Abstract

In the framework of quantum-chemical simulation (DFT) the structure was explored of six potentially probable tautomeric forms of 2-methyl-6-methoxy-3H-azepine and their relative thermodynamic stability was evaluated. In the tautomers obtained the preferred gradient channels are localized of [1,n]-H shifts capable of initiating their tautomerism. The most probable typical concerted reactions were analyzed of the formation of valence isomers, fused three-/six- and four-/five-membered carbo- and heterocycles, azabicyclo[4.1.0]hepta-2,4-dienes (azanorcaradienes) and azabicyclo[3.2.0]hepta-3,6-dienes respectively.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    V. A. Shagun, N. A. Nedolya, O. A. Tarasova & O. G. Volostnykh

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  1. V. A. Shagun
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  2. N. A. Nedolya
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  3. O. A. Tarasova
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  4. O. G. Volostnykh
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Correspondence to V. A. Shagun.

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Original Russian Text © V.A. Shagun, N.A. Nedolya, O.A. Tarasova, O.G. Volostnykh, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 5, pp. 728–744.

For Communication XIV, see [1].

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Shagun, V.A., Nedolya, N.A., Tarasova, O.A. et al. Heterocumulenes reactions with organometallic reagents: XV. Quantum-chemical investigatiom of skeleton rearrangements of 2-methyl-6-methoxy-3H-azepine originating from valence tautomerism. Russ J Org Chem 46, 722–739 (2010). https://doi.org/10.1134/S1070428010050222

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