95888-29-2Relevant articles and documents
Thermal decomposition of tert-butyl o-(phenoxy)- and o-(anilino)-phenyliminoxyperacetates
Calestani, Gianluca,Leardini, Rino,McNab, Hamish,Nanni, Daniele,Zanardi, Giuseppe
, p. 1813 - 1824 (2007/10/03)
Some o-phenoxy- and o-anilino-substituted aryliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The iminyls show no disposition to give 7-membered cyclisation on the phenyl group. In some cases, products have been found that can be rationalised through a 1,6-spirocyclisation of the iminyl radicals followed by homolytic 1,5-migration of the phenyl group from the aminic to the iminic nitrogen: this seems to be the first instance of such a process. Evidence has been found for the formation of imines through hydrogen abstraction by the iminyls; with two o-phenoxy-substituted peresters these imines have been unexpectedly isolated. The reactions have also afforded significant - in some cases major - amounts of other products (acridine, quinazolinone and indole derivatives) presumably deriving from carbon radicals: mechanisms are suggested to account for the formation of these compounds. The structure of the quinazolinone compound has been determined by X-ray crystallographic analysis.
The Reaction of Benzyne with Imines
Fishwick, Colin W. G.,Gupta, Ramesh C.,Storr, Richard C.
, p. 2827 - 2829 (2007/10/02)
The isolation of acridines from reaction of benzyne with the imines, N-benzylideneaniline and N-benzylidene-4-chloroaniline, and the amidines, N,N-dimethyl-N'-phenylformamidine and N-phenyliminomethylpyrrolidine, provides unambiguous evidence for the formation of transient benzazetidines by 2 + 2 cycloaddition.
