Jf. Mclellan et al., RING EXPANSION AND REARRANGEMENT REACTIONS OF N-HETEROARYLMETHYL RADICALS, Journal of the Chemical Society, Chemical Communications, (10), 1993, pp. 839-840
Flash vacuum pyrolysis of N-(p-chlorophenoxymethyl)azoles (e.g. 2 and
3) gives ring expanded products (e.g. 4 and 8) formed via N-heteroaryl
methyl radicals (e.g. 1 and 6); the mechanism of ring expansion genera
lly involves a novel 'walk'-rearrangement of the radical centre.