ACTION DU N-BROMOSUCCINIMIDE SUR LES DIOXOLANNES EN SERIE BICYCLOHEPTANIQUE. LIMITATION DES TRANSPOSITIONS DE WAGNER-MEERWEIN

Article abstract of DOI:10.1016/0040-4020(80)80151-7

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 rearrangement occur in methoxycarbonylbicyclo<2.2.1>heptane and in a bornanic compound respectively.