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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
[post]
2019
unpublished
O-Directed free radical hydrostannation of a β-cyclopropyl propargylic alcohol probe with stannanes and cat. Et<sub>3</sub>B in THF/H<sub>2</sub>O, or PhMe/MeOH, failed to deliver any detectable products of α-stannylvinyl cation capture. Instead only α-stannyl-β-cyclopropylvinyl radical intermediates could be detected, which underwent fast H-atom abstraction and/or cyclopropane ring-opening as a result of fast eliminative β-scission. These outcomes strongly rule against the claimed intermediacy
doi:10.26434/chemrxiv.8867651
fatcat:oubq3kgf2zftjfyudnizeiarl4