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The origin of the important M– CH3 ion in vinyl ethers has been elucidated through deuterium labelling; when a secondary hydrogen atom is available for transfer, 8-membered transition states play the dominant role and other hydrogen transfers, previously thought to be site-specific, have now been shown to involve randomization.
M. Katoh and C. Djerassi, J. Chem. Soc. D, 1969, 1385 DOI: 10.1039/C29690001385
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