Solvolysis of 2-(2-methoxyethyl)-3-methyl-2-cyclohexenyl p-nitrobenzoate

Add time:08/03/2019    Source:sciencedirect.com

In an attempt to study possible n-participation in allyl derivatives, 2-(2-methoxyethyl)-3-methyl-2-cyclohexenyl p-nitrobenzoate 4 was solvolyzed in various solvents including fluorinated alcohols. Its solvolysis rate is slower than that of the 2-butyl analog 3. This rate retardation can be explained by an electron-withdrawing inductive effect of methoxy group. The secondary α-deuterium isotope effect of ester 4 is normal in all the solvents investigated. These results show that the methoxy group does not assist the ionization of ester 4.

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