Detection and kinetics of the single-crystal to single-crystal complete transformation of a thiiranium ion into thietanium ion†‡
Abstract
The conversion of a di-tert-butyl-methylthiiranium ion into thietanium ion, that is reported in the literature as taking place spontaneously at 25 °C in a CD2Cl2 solution, has been discovered to occur quantitatively at room temperature (RT) also in the crystalline state. The ring enlargement reaction is accompanied, in the solid phase, by a modest deterioration of the quality of the sample under investigation, and all three specimens here studied by in situcrystallography maintained their single-crystal nature up to 100% conversion. The rearrangement reaction implies the breaking of a C–S bond and the formation of a new bond of the same type, together with the migration of a