A novel method of remotely triggering a cyclopropyl carbinyl to homo-allyl radical fragmentation process

A series of model compounds were prepared in order to investigate the conditions that would favour the formation of a cyclopropyl carbinyl radical via a 1,5 hydrogen atom translocation process. The models varied in the degree of unsaturation adjacent to the cyclopropyl carbinyl position and it was found that the 1,5 hydrogen atom radical translocation process was favoured only when alternative cyclisation pathways were not possible.