Thermal decomposition of the tert-butyl perester of thymidine-5'-carboxylic acid carried out at 85 °C in different solvents affords the tert-butylacetal, deriving from in cage decomposition, and pseudo C4'-radicals. These latter can be reduced to by hydrogen atom abstraction from thiol (thiophenol or glutathione) or THF, or can be oxidized to cations by dioxygen or perester itself. Cations are stereoselectively trapped by the nucleophilic solvent (tert-butanol, methanol, water) to give acetals the corresponding acetals.
P. C. Montevecchi, A. Manetto, L. Navacchia, C. Chatgilialoglu (2004). Thermal decomposition of the tert-butyl perester of thymidine-5'-carboxylic acid. Formation and fate of the pseudo-C4'-radical. TETRAHEDRON, 60, 4303-4308 [10.1016/j.tet.2004.03.029].
Thermal decomposition of the tert-butyl perester of thymidine-5'-carboxylic acid. Formation and fate of the pseudo-C4'-radical
MONTEVECCHI, PIER CARLO;
2004
Abstract
Thermal decomposition of the tert-butyl perester of thymidine-5'-carboxylic acid carried out at 85 °C in different solvents affords the tert-butylacetal, deriving from in cage decomposition, and pseudo C4'-radicals. These latter can be reduced to by hydrogen atom abstraction from thiol (thiophenol or glutathione) or THF, or can be oxidized to cations by dioxygen or perester itself. Cations are stereoselectively trapped by the nucleophilic solvent (tert-butanol, methanol, water) to give acetals the corresponding acetals.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
