Thiol-Olefin Cooxidation (TOCO) Reaction. 10. Phenyl Allyl Ether and p-Chlorothiophenol

Article abstract of DOI:10.1021/jo00385a017

The TOCO reaction of a hexane solution of phenyl allyl ether and p-chlorothiophenol was investigated under photochemical and thermal activation conditions and over a temperature range of -23 to +25 deg C.The formation of the desired TOCO product, the thiol-olefin anti-Markovnikov adduct, and p-bis(chlorophenyl) sulfide was found to vary both as a function of temperature and of the activating conditions.The equilibrium constants for the formation of the thiol-olefin complexes were determined in the case of phenyl allyl ether and the analogous 4-phenyl-1-butene as well as 1-octene, norbornene, and 1-phenylbutane in order to elucidate the nature of these associations.