Neighboring methoxy group effect in solvolysis reactions of cyclopentyl and cyclohexyl p-toluenesulfonates

摘要

In an earlier paper from this laboratory, we investi- gated the neighboring-group effect of a methoxy sub- stituent upon the rates of solvolysis of trans-2-methoxy- cyclopentyl p-toluenesulfonate (1) and trans-2-methoxy- cyclohexyl p-toluenesulfonate (2). Although we found that the presence of a rans-2-methoxy group retarded the rate of solvolysis of both the cyclopentyl and cyclo- hexyl systems, it was observed that this rate retardation was insensitive to change from acetic acid (a solvent known to promote k_s solvolysis for cyclohexyl tosylate~2a-e) to trifuoroacetic acid ( a solvent known to promote kΔ solvolysis for secondary tosylates~2a-d).