TY - JOUR A1 - Dell, A A1 - Johnson, BL T1 - Acetolysis of endo-5-Methyltricyclo-[2,2,1,02,6]hept-exo-3-yl and endo-5-Methyltricyclo[2,2,1,02,6]hept-endo-3-yl p-Bromobenzenesulfonates JF - Australian Journal of Chemistry JO - Aust. J. Chem. Y1 - 1979 VL - 32 IS - 10 SP - 2215 EP - 2221 KW - UR - https://doi.org/10.1071/CH9792215 N2 - Acetolyses of the title compounds (4b) and (5b) at 25·7º proceed with steady first-order kinetics and with comparable rate constants. Some isomerization of (5b) to (4b) occurred during acetolysis of (5b). The products derived from acetolysis of each p-bromobenzenesulfonate were comparable and included endo-5-methyltricycl0[2,2,1,02,6]hept-exo-3-yl acetate (4c), endo-5-methyltricyclo- [2,2,1,02,6]hept-endo-3-yl acetate (5c), endo-3-methylbicyclo[2,2,1]hept-5-en-exo-2-yl acetate (6) and anti-7-methylbicyclo[2,2,1]hept-5-en-exo-2-yl acetate (7). These results are rationalized in terms of a reaction mechanism involving isomerization of the endo to the exo intimate ion pair, (10) to (ll), as well as a capturable intermediate carbocation which is common to the acetolysis of both p-bromo- benzenesulfonates. ER -