Journal
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Volume -, Issue 9, Pages 1072-1078Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b009843o
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Some ortho-(phenylsulfanyl)- and ortho-(phenylsulfonyl)-substituted phenyliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The sulfanyl-substituted iminyls showed no tendency to give either 1,7- or 1,6-ring closure onto the S-phenyl ring. They gave instead 1,5-cyclisation onto the sulfur atom with release of a phenyl radical and formation of benzoisothiazoles. This seems to be the first example of S(H)i reaction of a nitrogen-centred radical at a sulfide moiety. On the other hand, the sulfonyl-substituted iminyl underwent 1,6-cyclisation to a small extent, furnishing a phenanthridine through an unprecedented 1,5-aryl radical migration from sulfur to nitrogen followed by loss of sulfur dioxide and ring closure of an aryl radical.
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