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Synlett 1999; 1999(12): 1978-1980
DOI: 10.1055/s-1999-2971
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Generation and Capture of Iminyl Radicals from Ketoxime Xanthates

Fabien Gagosz* , Samir Z. Zard
  • *Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France; Fax + 33(0)1 69 33 30 10; E-mail: sam.zard@icsn.cnrs-gif.fr
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Publication Date:
31 December 1999 (online)

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Irradiation of ketoxime O-(S-methyl xanthates) containing a γ,δ-double bond leads to a dihydropyrrole through cyclisation of an intermediate iminyl radical in a radical chain reaction. The last propagation step involves transfer of a dithiocarbonate group and various external radical traps can be incorporated into the medium, allowing access to a variety of substituted dihydropyrroles.

iminyl radicals - 5 exo cyclisation - dihydropyrroles