Abstract
AbstractThe pyrolyses of four alkyl allyl sulfides with substituents on the αC atom of the alkyl moiety have been studied in a stirred‐flow system over the temperature range 340‐400°C and pressures between 2 and 12 torr. The only products formed are propene and thioaldehydes. The reactions showed first‐order kinetics with the rate coefficients following the Arrhenius equations: Chloromethyl allyl sulfide: Cyanomethyl allyl sulfide: 1‐cyanoethyl allyl sulfide: Neopentyl allyl sulfide: The effects of these and other substituents on the reactivity is discussed in relation with the stabilization of a polar six‐centered transition state. The results support a non‐concerted mechanism where the 1–5 αH atom shift is assisted by its acidic character.
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