Synthesis and reactions of allylic azides of the adamantane series
- Authors: Leonova M.V.1, Baimuratov M.R.1, Klimochkin Y.N.1
-
Affiliations:
- Samara State Technical University
- Issue: Vol 59, No 11 (2023)
- Pages: 1455-1464
- Section: Articles
- URL: https://journals.rcsi.science/0514-7492/article/view/247257
- DOI: https://doi.org/10.31857/S0514749223110071
- EDN: https://elibrary.ru/NDPWNK
- ID: 247257
Cite item
Abstract
A mixture of nucleophilic substitution product and isomeric azide resulting from [3,3]-sigmatropic rearrangement was obtained by interaction of allyl bromides of adamantane series with sodium azide. Epoxidation reactions of allylic azides of the adamantane series were investigated. The reduction of the obtained trans -2-(adamantan-1-yl)-3-(azidomethyl)oxirane with lithium alumohydride synthesized ( S *)-(adamantan-1-yl)[( S *)-aziridin-2-yl]methanol which, when heated with hydrochloric acid, gives the product of the aziridine ring opening is (1 S *,2 R *)-1-(adamantan-1-yl)-3-chloro-1-hydroxypropan-2-amino chloride.
About the authors
M. V. Leonova
Samara State Technical University
Email: mvleon@mail.ru
M. R. Baimuratov
Samara State Technical University
Yu. N. Klimochkin
Samara State Technical University
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