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.
|Media of output||ChemRxiv Database|
|Number of pages||4|
|Publication status||Published - 15 Jul 2019|
|Publisher||American Chemical Society|
- 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