Gas-phase generation and cyclisation reactions of imidoyl radicals?

Organic & Biomolecular Chemistry Pub Date: 2011-11-24 DOI: 10.1039/C1OB06228J

Abstract

Some 1,2-diarylimidoyl radicals were generated in the gas-phase by intramolecular radical translocation from ortho-imino-aryloxyl radicals, in turn generated under flash vacuum pyrolysis (FVP) conditions. The imidoyls reacted with XRortho′-substituents in the N-aryl group to give (in most cases) modest yields of cyclisation products. Depending on the nature of the bridging atom (X), the formation of these products was initiated either by a further hydrogen atom translocation (X = CH2), or by ipso-attack onto the aryl group (R = Ph), or by direct substitution at the heteroatom (X = S). With XR = N(Me)Ph, the major reaction product was probably the result of a competing pathway not involving the corresponding imidoyl.

Graphical abstract: Gas-phase generation and cyclisation reactions of imidoyl radicals
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