Fast ring-opening of an intermediary α-stannyl-β-cyclopropylvinyl radical does not support formation of an α-stannylvinyl cation in the O-directed free radical hydrostannation of dialkyl acetylenes

Hamish A. Watson; Soraya Manaviazar; Hannah G. Steeds; Karl J. Hale

doi:10.1039/C9CC05492H

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Fast ring-opening of an intermediary α-stannyl-β-cyclopropylvinyl radical does not support formation of an α-stannylvinyl cation in the O-directed free radical hydrostannation of dialkyl acetylenes†

Hamish A. Watson,^a Soraya Manaviazar,^a Hannah G. Steeds^a and Karl J. Hale

*^a

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* Corresponding authors

^a The School of Chemistry and Chemical Engineering, Queen's University Belfast, Stranmillis Road, Belfast BT9 5AG, Northern Ireland, UK
E-mail: k.j.hale@qub.ac.uk

Abstract

O-directed hydrostannation of β-cyclopropyl propargyl alcohol 22 with stannanes and cat. Et₃B in THF/H₂O or PhMe/MeOH fails to deliver any detectable products of α-stannylvinyl cation capture. Instead only α-stannyl-β-cyclopropylvinyl radical intermediates can be detected, which undergo fast H-atom abstraction and/or cyclopropane ring-opening as a result of eliminative β-scission.

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Article information

DOI: https://doi.org/10.1039/C9CC05492H
Article type: Communication
Submitted: 18 Jul 2019
Accepted: 21 Oct 2019
First published: 15 Nov 2019
This article is Open Access

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Chem. Commun., 2019,55, 14454-14457

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Fast ring-opening of an intermediary α-stannyl-β-cyclopropylvinyl radical does not support formation of an α-stannylvinyl cation in the O-directed free radical hydrostannation of dialkyl acetylenes

H. A. Watson, S. Manaviazar, H. G. Steeds and K. J. Hale, Chem. Commun., 2019, 55, 14454 DOI: 10.1039/C9CC05492H

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Chemical Communications

Fast ring-opening of an intermediary α-stannyl-β-cyclopropylvinyl radical does not support formation of an α-stannylvinyl cation in the O-directed free radical hydrostannation of dialkyl acetylenes†

Abstract

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Fast ring-opening of an intermediary α-stannyl-β-cyclopropylvinyl radical does not support formation of an α-stannylvinyl cation in the O-directed free radical hydrostannation of dialkyl acetylenes

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