Tetrahedron p. 2745 - 2755 (1980)
Update date:2022-08-04
Topics:
Bazbouz, Akram
Christol, Henri
Coste, Jacques
Plenat, Francoise
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.
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(1982)
