THERMAL-DECOMPOSITION OF TERT-BUTYL O-(PHENOXY)-PHENYLIMINOXYPERACETATES AND O-(ANILINO)-PHENYLIMINOXYPERACETATES

Some o-phenoxy- and o-anilino-substituted aryliminyl radicals have bee n generated by thermal decomposition of suitable tert-butyl iminoxyper acetates. The iminyls show no disposition to give 7-membered cyclisati on on the phenyl group. In some cases, products have been found that c an be rationalised through a 1,6-spirocyclisation of the iminyl radica ls followed by homolytic 1,5-migration of the phenyl group from the am inic to the iminic nitrogen: this seems to be the first instance of su ch a process, Evidence has been found for the formation of imines thro ugh hydrogen abstraction by the iminyls; with two o-phenoxy-substitute d peresters these imines have been unexpectedly isolated. The reaction s have also afforded significant-in some cases major-amounts of other products (acridine, quinazolinone and indole derivatives) presumably d eriving from carbon radicals: mechanisms are suggested to account for the formation of these compounds. The structure of the quinazolinone c ompound has been determined by X-ray crystallographic analysis.