1-Phenyl-1-halo-1-silacyclohexanes
- Authors: Suslova E.N.1, Shainyan B.A.1
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Affiliations:
- Favorsky Irkutsk Institute of Chemistry, Siberian Branch
- Issue: Vol 86, No 8 (2016)
- Pages: 1854-1858
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/215935
- DOI: https://doi.org/10.1134/S1070363216080132
- ID: 215935
Cite item
Abstract
The approaches to synthesis of 1-phenyl-1-halo-1-silacyclohexanes C5H10Si(Ph)X (X = F, Cl, Br) have been examined. 1-Phenyl-1-chloro-1-silacyclohexane has been prepared via the known reaction of phenyltrichlorosilane with dimagnesium derivative of 1,5-dibromopentane; up to 20% of 1-bromo-1-phenyl-1-silacyclohexane admixture is formed along with the target product. The minor product formation has been prevented using an alternative method of chlorination of 1-phenyl-1-silacyclohexane with N-chlorosuccinimide. 1-Phenyl-1-fluoro-1-silacyclohexane has been obtained in close to quantitative yield via the reaction of 1-phenyl-1-chloro-1-silacyclohexane with SbF3 and in 70% yield via its reaction with HF. The synthesis of 1-phenyl-1-bromo-1-silacyclohexane via bromination of 1-phenyl-1-chloro-1-silacyclohexane with N-bromosuccinimide has given the target product as a minor one, the major product being disiloxane formed due to hydrolysis of the Si–Br bond.
About the authors
E. N. Suslova
Favorsky Irkutsk Institute of Chemistry, Siberian Branch
Email: bagrat@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
B. A. Shainyan
Favorsky Irkutsk Institute of Chemistry, Siberian Branch
Author for correspondence.
Email: bagrat@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
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