Neighboring group participation by oxygen in the solvolysis of acyclic. gamma.-alkoxy substituted p-toluenesulfonates

EL Eliel, L Clawson, DE Knox

Index: Eliel, Ernest L.; Clawson, Leigh; Knox, David E. Journal of Organic Chemistry, 1985 , vol. 50, # 15 p. 2707 - 2711

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Citation Number: 22

Abstract

Methanolysis of branched 3-(benzyloxy) propyl p-toluenesulfonates, PhCH20CR1R2CR3R4CHR50Ts (R'= Me, R2-R5= H; R'= R2= Me, R3-R5= H; R1= R2= RS= Me, R3= R4= H; R1= R2= R4= R5= H, R3= M e; R1= R2= R5= H, R3= R4= Me) proceeds with partial rearrangement, implying neighboring group participation, only when there are geminal methyl groups in the 2-or 3-position (R3= R4= Me or R'= R2= Me). ...