Xanthates derived from 1,3-dithiane and its monosulfoxide; one-carbon radical equivalents

Michiel de Greef (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

The behaviour and synthetic scope of the C-2 centred radicals derived from 1,3-dithiane and 1,3-dithiane 1-oxide have been studied. Both radicals are available from the corresponding xanthates and have proved suitable substrates for the xanthate transfer reaction. However, the synthetic scope of the former is severely limited by the fact that it does not add to unactivated olefins. The latter on the other hand is a more promising radical precursor and undergoes smooth radical addition to a wide range of alkenes. Furthermore, subsequent transformations of some of the radical adducts confirm its utility as a synthetic equivalent of both the methyl and the formyl radical. © 2004 Elsevier Ltd. All rights reserved.

Michiel de Greef, Samir Z. Zard. Xanthates derived from 1,3-dithiane and its monosulfoxide; one-carbon radical equivalents. Tetrahedron, 2004, 60 (35), pp.7781-7791. ⟨10.1016/j.tet.2004.06.061⟩. ⟨hal-00954819⟩