engleski

Solvolysis of 3-alkenyl-2-cyclohexenyl esters

In an attempt to study possible -participation in allyl derivatives, 3-alkenyl-5, 5-dimethyl-2-cyclohexenyl p- nitrobenzoates and 2-alkenyl-3-methyl-2-cyclohexenyl p-nitrobenzoates were solvolyzed in 97 wt % trifluoroethanol and 80 vol % ethanol. Water soluble 1-methyl-3-(3-alkenyl-5, 5-dimethyl-2-cyclohexenyl) pyridinium iodides 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 -deuterium isotope effects (kH/kD = 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

3-alkenyl-2-cyclohexenyl esters ; solvolysis

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