Journal of Organic Chemistry p. 92 - 95 (1981)
Update date:2022-08-25
Topics:
Schiavelli, Melvyn D.
Jung, Dorothy M.
Vaden, Anne Keller
Stang, Peter J.
Fisk, Thomas E.
Morrison, David S.
The solvolytic reactivity of a number of silicon- and alkynyl-substituted vinyl triflates was investigated in aqueous ethanol.Activation parameters and solvent m values were determined for all subtrates.Relative rate data show that the Me3Si group is accelerating and hence stabilizing relative to hydrogen but destabilizing relative to a t-Bu group.The α-ethynyl substituent causes a rate decrease compared to a methyl group despite its ?-donating resonance ability.These results are discussed.
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