77299-93-5Relevant academic research and scientific papers
REACTION DU N-BROMOSUCCINIMIDE SUR LES ARYL-2 DIOXOLANNES-1,3 DEROULEMENT DE LA REACTION
Bazbouz, Akram,Christol, Henri,Coste, Jacques,Plenat, Francoise
, p. 1955 - 1960 (2007/10/02)
Reaction of NBS with 1,3-dioxolanes fused to a bicyclo skeleton involves two intermediates, the dioxolanylium ion and the 2-succinimido-1,3-dioxolane.Evidence is presented that the unusual stability of the former ionic species is due to the steric
ACTION DU N-BROMOSUCCINIMIDE SUR LES DIOXOLANNES EN SERIE BICYCLOHEPTANIQUE. LIMITATION DES TRANSPOSITIONS DE WAGNER-MEERWEIN
Bazbouz, Akram,Christol, Henri,Coste, Jacques,Plenat, Francoise
, p. 2745 - 2755 (2007/10/02)
Vicinal benzoyloxy-trans-bicycloheptanic 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 methoxycarbonylbicycloheptane and in a bornanic compound respectively.
