Ring size effects in the neophyl rearrangement. VIII. Synthesis and solvolysis of 1-methyl-2, 3-benzocycloalkenylcarbinyl tosylates

JW Wilt, WW Pawlikowski Jr…

Index: Wilt,J.W. et al. Journal of Organic Chemistry, 1972 , vol. 37, # 6 p. 820 - 825

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Abstract

l-Methyl-2, 3-benzocycloalkenylcarbinyl tosylates 5 were synthesized and their solvolytic reactivity wm determined. Neither in acetolysis nor in hydrolysis in 60% acetone was a ring size effect of any significance evidenced. The reactivities mirrored those of the unmethylated analogs 3. Products from 5 were totally rearranged via aryl ring migration indicating that aryl participation was essentially the only solvolysis pathway. The opposing factors in 3 of ...