Radical rearrangements

摘要

A multinational team led by Anna Chrostowska (University of Pau, France), Stanislaw Lesniak (University of Lodz, Poland) and Curt Wentrup (University of Queenland) have reported new free radical rearrangement reactions induced by flash vacuum thermolysis of N-t-butylimines (Vu T.Y., Chrostowska A., Justyna K., Pasternak B., Lesniak S., Wentrup C. Chem. Eur. J. 2013, 19, 14983-8). Efficient methyl group loss from the t-butyl groups affords iminoalkyl radicals, which can undergo 1,4-H shifts followed by cyclisation to isoquinolines, or onto the N atom of a pyridine ring to afford an imidazo[l,5-a]pyridine.