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Synthesis and Reactions of Allylic Azides of the Adamantane Series

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Abstract

A mixture of a nucleophilic substitution product and its isomeric azide resulting from [3,3]-sigmatropic rearrangement was obtained as a result of the reaction of hindered bromides of the adamantane series with sodium azide. Epoxidation reactions of allylic azides of the adamantane series were investigated. The reduction of the syntesized trans-2-(adamantan-1-yl)-3-(azidomethyl)oxirane with lithium alumohydride gave (S*)-(adamantan-1-yl)[(S*)-aziridin-2-yl]methanol. Under heating with HCl, the latter underwent aziridine ring opening to form (1S*,2R*)-1-(adamantan-1-yl)-3-chloro-1-hydroxypropan-2-aminium chloride.

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Funding

The work was financially supported by the Russian Science Foundation (project no. 21-73-20103). The spectral data were obtained with the support of the Ministry of Science and Higher Education of the Russian Federation (subject no. FSSE-2023-0003) in the framework of the state assignment for the Samara State Technical University.

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Authors and Affiliations

  1. Samara State Technical University, 443100, Samara, Russia

    M. V. Leonova, M. R. Baimuratov & Yu. N. Klimochkin

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  1. M. V. Leonova
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  2. M. R. Baimuratov
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Correspondence to M. V. Leonova.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1455–1464 https://doi.org/10.31857/S0514749223110071.

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Leonova, M.V., Baimuratov, M.R. & Klimochkin, Y.N. Synthesis and Reactions of Allylic Azides of the Adamantane Series. Russ J Org Chem 59, 1892–1900 (2023). https://doi.org/10.1134/S1070428023110076

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