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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Formation of a methide derivative upon photolysis of thymidine bromohydrins
Thierry Douki1, Guillaume Vadesne-Bauer, Jean Cadet
1Laboratoire Lésions des Acides Nucléiques, Service de Chimie Inorganique et Biologique, UMR 5046, CEA/DSM/Département de Recherche Fondamentale sur la Matière Condensée, CEA-Grenoble, France. tdouki@cea.fr
Abstract:
Reaction of bromine with thymidine in aqueous solution produces, in high yield, the corresponding 5-bromo-6-hydroxy-5,6-dihydroderivative (thymidine bromohydrins). UVC photolysis of thymidine bromohydrins gives rise to a reactive intermediate that is converted into 5-(hydroxymethyl)-2'-deoxyuridine upon incubation in water. When the former compound is left in methanol, ethanol, or propanol, the corresponding 5-alkoxymethyl derivatives are produced. The proposed structure for the primary photolysis product of thymidine bromohydrins is a methide derivative of the thymine ring. This compound could be an interesting intermediate in the synthesis of methyl-substituted thymidine.
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