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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