Mechanism of Protodephenylation of 1,3-Silaheterocyclohexanes. Effect of Heteroatom
- Authors: Kirpichenko S.V.1, Albanov A.I.1, Shainyan B.A.1
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Affiliations:
- A.E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- Issue: Vol 88, No 1 (2018)
- Pages: 96-102
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/221954
- DOI: https://doi.org/10.1134/S1070363218010152
- ID: 221954
Cite item
Abstract
The mechanism of electrophilic cleavage of the Si–Ph bond in 1,3-silaheterocyclohexanes is investigated. 3-Aryl-3-silatetrahydropyrans are shown to be less prone to the cleavage of the Si–Ph bond under the action of trifluromethanesulfonic acid than the corresponding 3-silathianes or silacyclohexanes. The effect of heteroatom (N, O, S) in the ring on the functionalization at the silicon atom in 1,3-silaheterocyclohexanes was studied experimentally by the method of NMR spectroscopy and theoretically by DFT calculations and the mechanism was suggested of dephenylation as a function of the nature of heteroatom.
About the authors
S. V. Kirpichenko
A.E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: bagrat@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
A. I. Albanov
A.E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: bagrat@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
B. A. Shainyan
A.E. Favorskii 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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