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 language | English |
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Type | Preprint |
Media of output | ChemRxiv Database |
Number of pages | 4 |
Publication status | Published - 15 Jul 2019 |
Publication series
Name | ChemRxiv |
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Publisher | American 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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Dive into the research topics of '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'. Together they form a unique fingerprint.Student theses
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Further investigations into the mechanism of the o-directed free radical hydrostannation of alkyl and aryl acetylenes
Watson, H. (Author), Stevenson, P. (Supervisor) & Hale, K. (Supervisor), Jul 2022Student thesis: Doctoral Thesis › Doctor of Philosophy
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