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The "parent" tertiary alkyl chloroformate, tert -butyl chloroformate, is unstable, but the tert -butyl chlorothioformate ( 1 ) is of increased stability and a kinetic investigation of the solvolyses is presented. Analyses in terms of the simple and extended Grunwald-Winstein equations are carried out. The original one-term equation satisfactorily correlates the data with a sensitivity towards changes in solvent ionizing power of 0.73 ±0.03. When the two-term equation is applied, the sensitivity towards changes in solvent nucleophilicity of 0.13 ± 0.09 is associated with a high (0.17) probability that the term that it governs is not statistically significant.

Correlation of the rates of solvolysis of tert-butyl chlorothioformate and observations concerning the reaction mechanism