HYDROGENOLYSIS OF CARBON-FLUORINE BONDS IN CATALYTIC-HYDROGENATION

In contrast to the strong stability of saturated fluorine compounds in catalytic hydrogenation, allylic and vinylic fluorine atoms are displace by hydrogen relatively readily. Hydrogenolysis of carbon-fluorine bonds accompanies addition of hydrogen across double bonds in methyl 4-fluoro-3-methyl-2-pentenoate, in fluoromaleic, fluorofumaric, difluoromaleic and difluorofumaric acids. The extent of hydrogenolysis is affected by the catalyst and by the solvent. A concerted mechanism is offered to explain the readiness of the hydrogenolysis in allylic and vinylic fluorides. © 1979.