Collect. Czech. Chem. Commun. 2002, 67, 1325-1334

Synthesis of α-Fluoro-β-lactones and Their Thermal Conversion to 1-Fluoroalkenes

Rogelio Ocampoa, William R. Dolbier, Jr.b,* and Fabio Zuluagac

a Departamento de Química, Universidad de Caldas, Manizales, Colombia
b Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.
c Departamento de Química, Universidad del Valle, Cali, Colombia


α-Fluoro-β-lactones have been synthesized and isolated for the first time from α-fluoro-β-hydroxy acids by using the couple TsCl/DMAP as lactonization agent. A detailed description of the synthesis and spectroscopic properties of α-fluoro-β-lactones is presented. Preliminary results indicate that thermolysis of these new β-lactones produces 1-fluoroalkenes.

Keywords: β-Lactones; Fluorine; Fluoroalkenes; Decarboxylation; Thermolysis; Hydroxy acids; Alkenes.

References: 52 live references.