title: From a remarkable manifestation of polar effects in a radical fragmentation to the convergent synthesis of highly functionalized ketones.
abstract: A new radical addition/C-C bond fragmentation process is reported. Vinyl carbinols derived from 2-methyl-2-phenylpropanal react with radicals generated from xanthates to give the corresponding ketones. The radical cleavage reaction proceeds under mild conditions, in good to high yield, and in the presence of the unprotected carbinol. Highly functionalized 1,5-diketones and pyridines are readily available using this approach.
authors: Laboratoire de Synthèse Organique, CNRS UMR 7652 Ecole Polytechnique, 91128 Palaiseau Cedex, France. debien@dcso.polytechnique.fr
authors: Laurent
authors: L
authors: Debien
authors: Samir Z
authors: SZ
authors: Zard
mesh_terms: D005609:Free Radicals / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D014970:Xanthines / Q000737:chemistry*
chemical_list: D005609:Free Radicals; D007659:Ketones; D014970:Xanthines