Thermal Transformations of Allyl Phenyl Sulfide: A Quantum-Chemical Study

The transformation routes of allyl phenyl sulfide are calculated within the density functional theory (B3PW91/6-31G** quantum chemical approximation). We found that the chair conformation is a transition state of the first stage (the conversion of allyl phenyl sulfide into 6-(prop-2-en-1-yl)cyclohex-2,4-dien-1-thione). The second stage involves the interaction between thione and either allyl phenyl sulfide and allyl thiophenol molecule or with a second thione molecule. The cyclization of allyl thiophenol implies the formation of methyl thiocumaran. The thermal isomerization of allyl phenyl sulfide to propenyl phenyl sulfide is improbable.