Chemistry of the β?Thiolactones: Substituent and Solvent Effects on Thermal Decomposition and Comparison with the β?Lactones.

摘要

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.