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

Research output: Other contribution

2 Citations (Scopus)

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.
Original languageEnglish
TypePreprint
Media of outputChemRxiv Database
Number of pages4
Publication statusPublished - 15 Jul 2019

Publication series

NameChemRxiv
PublisherAmerican Chemical Society

Keywords

  • Stannylvinyl Cation
  • O-Directed Free Radical Hydrostannation with Ph3SnH/cat. Et3B, Propargylically-Oxygenated Alkyl Acetylenes, Stannylvinyl Radical, b-Stannylvinyl cation, Vinylperoxy radical, Trisubstituted Stannylvinyl Radical H-Atom Abstraction, Vinylstannane isomerisation, Allylic 1,3-strain and 1,2-strain, Internal Ligand Enhanced Radicalophilicity, Ph3Sn radicals have higher electron affinity, The magnitudes of polar solvent rate accelerations observed for genuinely ionic reaction mechanisms

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