Chemistry of the β-thiolactones: substituent and solvent effects on thermal decomposition and comparison with the β-lactones.
The synthesis of a series of di-, tri-, and tetraalkyl β-thiolactones and β-lactones is described as well as their thermal decomposition with extrusion of carbon oxysulfide and carbon dioxide in two solvents of opposite polarities. The β-thiolactones are considerably more thermally stable than the β-lactones and require higher temperatures for efficient decomposition in both solvents, whatever the degree of substitution. The results are interpreted in terms of a zwitterionic mechanism for fragmentation with a change in the rate-determining step between the two series.
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS , Avenue de la Terrasse, 91190 Gif-sur-Yvette, France.
Amandine
A
Noel
Bernard
B
Delpech
David
D
Crich
D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D012997:Solvents / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature
D007783:Lactones; D012997:Solvents; D013438:Sulfhydryl Compounds