Issue 3, 2012

Gas-phase generation and cyclisation reactions of imidoyl radicals

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

Article information

Article type
Paper
Submitted
22 Jul 2011
Accepted
06 Oct 2011
First published
24 Nov 2011

Org. Biomol. Chem., 2012,10, 623-630

Gas-phase generation and cyclisation reactions of imidoyl radicals

R. Leardini, H. McNab, D. Nanni, A. G. Tenan and A. Thomson, Org. Biomol. Chem., 2012, 10, 623 DOI: 10.1039/C1OB06228J

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