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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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 languageEnglish
Number of pages4
JournalChemical Communications
DOIs
Publication statusPublished - 15 Nov 2019

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Alkynes
Acetylene
Free radicals
Free Radicals
Cations
Alcohols
Positive ions
Atoms
propargyl alcohol
cyclopropane
stannane

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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 = "11",
day = "15",
doi = "10.1039/c9cc05492h",
language = "English",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",

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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 -