Action du N-bromosuccinimide sur les dioxolannes en série bicyclo [2.2.1 ]heptanique. Limitation des transpositions de wagner-meerwein

Vicinal benzoyloxy-trans-bicyclo 2.2.1] heptanic bromhydrins, otherwise difficult to obtain are formed from N-bromosuccinimide and norbornanes bearing a 2-aryl-1,3 dioxolane skeleton. The greater stability of the intermediate dioxolenium ion reduces the tendency towards both Wagner-Meerwein rearrangement and neighbouring group participation by chlorine, processes usually observed when a less stable intermediate is involved. Nevertheless, methoxycarbonyl neighbouring group participation and Wagner Meerwein rearrangment occur in methoxycarbonylbicyclo 2.2.1]heptane and in a bornanic compound respectively.