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

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

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article

69 Downloads (Pure)

Abstract

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

Original language	English
Number of pages	4
Journal	Chemical Communications
DOIs	https://doi.org/10.1039/c9cc05492h
Publication status	Published - 15 Nov 2019

Access to Document

10.1039/c9cc05492hLicence: CC BY

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
Copyright 2019 the authors. This is an open access article published under a Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 2.9 MBLicence: CC BY

Fingerprint Dive into the research topics of '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'. Together they form a unique fingerprint.

Cite this

Watson, H. A., Manaviazar, S., Steeds, H. G., & Hale, K. J. (2019). 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. Chemical Communications. https://doi.org/10.1039/c9cc05492h

@article{71bbcc970d24424b880c3179a82f7073,

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

author = "Watson, {Hamish A} and Soraya Manaviazar and Steeds, {Hannah G} and Hale, {Karl J}",

year = "2019",

month = nov,

day = "15",

doi = "10.1039/c9cc05492h",

language = "English",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

}

TY - JOUR

T1 - 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

AU - Watson, Hamish A

AU - Manaviazar, Soraya

AU - Steeds, Hannah G

AU - Hale, Karl J

PY - 2019/11/15

Y1 - 2019/11/15

N2 - O-Directed hydrostannation of b-cyclopropyl propargyl alcohol 22 with stannanes and cat. Et3B in THF/H2O or PhMe/MeOH fails todeliver any detectable products of α-stannylvinyl cation capture. Instead only α-stannyl-β-cyclopropylvinyl radical intermediates canbe detected, which undergo fast H-atom abstraction and/or cyclopropane ring-opening as a result of eliminative β-scission.

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

U2 - 10.1039/c9cc05492h

DO - 10.1039/c9cc05492h

M3 - Article

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

ER -