| Abstract: | The reaction of 2-methylnorborn-2-ene with N-bromosuccinimide produced exo-3-bromo-2-methylenenorbornane and 2-methyl-3-bromonortricyclene in a 3:1 ratio. No 2-bromomethyl-norborn-2-ene was found. Most of the unreacted olefin was found to be isomerized to 2-methylenenorbornane. The hydrolysis of 2-methyl-3-bromo-nortricyclene with silver acetate in a 50% mixture of acetone and water afforded the corresponding alcohol and acetate. Exo-3-bromo-2-methylenenorbornane on similar treatment gave the exo-3-hydroxy-2-methylene-norbornane and 2-hydroxymethyl-norbornane and 2-hydroxymethyl-norborn-2-ene and their corresponding acetates in a 3:2 ratio. An ionic rather than a radical mechanism is proposed for the bromination reaction. In the solvolysis reactions of the resulting bromides the nature of the ionic intermediates is discussed. |
