Solvolysis of 3-alkenyl-2-cyclohexenyl estrs

Add time:08/01/2019    Source:sciencedirect.com

In an attempt to study possible π -participation in allyl derivatives, 3-alkenyl-5,5-dimethyl-2-cyclohexenyl p-nitrobenzoates 4 and 2-alkenyl-3-methyl-2-cyclohexenyl p-nitrobenzoates 5 were solvolyzed in 97 wt % trifluoroethanol and 80 vol % ethanol. Water soluble 1-methyl-3-(3-alkenyl-5,5-dimethyl-2-cyclohexenyl) pyridinium iodides 6 were solvolyzed in water and in aqueous solvents, as well as under micellar conditions. All esters show in each of the solvents normal values of secondary α-deuterium isotope effects (kHkD = 1.17–1.23). Also in comparison to saturated analogues the investigated esters show a lower solvolytic reactivity. On the basis of these results it was concluded that the solvolysis proceeds via a stepwise mechanism involving a resonance-stabilized cyclohexenyl cation as the reaction intermediate.

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