Clean radical-induced isomerisation of homoadamantane to 1- and 2-methyladamantane
Abstract
Homoadamantane slowly rearranges at 400 °C to a mixture of 1- and 2-methyladamantane (ca. 2.5:1 ratio) in a reaction which is accelerated by a radical initiator. The products from rearrangement of [4-13C]-, [4,4-D2]-, and [3,6-D2]- homoadamantane are consistent with mechanisms involving initiation by abstraction of hydrogen from the 3- and 4-position of homoadamantane, rearrangement by elimination-readdition in the radicals formed, and chain transfer through hydrogen abstraction by the 1- and 2-adamantylmethyl radicals.