Abstract
Thermal decomposition of n-butyl thiolochloroformate at 150°C follows a similar pattern to that reported previously for n-butyl chloroformate, to give butyl chloride which is largely rearranged to the s-butyl isomer. An ion-pair mechanism, involving 1,2- and 1,3-hydride shifts, is proposed. The less stable thiono- and dithio-chloroformates decompose to give lower yields of butyl chlorides (mainly without rearrangement) together with numerous other byproducts, indicating the operation of a more complex combination of reaction pathways. The mass spectra of all three thio compounds exhibit molecular ions; the most prominent fragment ions in their spectra are the n-butyl cation, and the radical cations COS+ • and CS2 + •. Numerous chlorine-containing ions of low intensity are also observed, and their mode of formation is discussed. GRAPHICAL ABSTRACT
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