SULFENE MECHANISM IN THE PYRIDINE-CATALYZED REACTIONS OF ALKANESULFONYL HALIDES WITH PHENOLS

The influence of pyridine bases upon the rate and mechanism of the int eraction of alkanesulfonyl halides with phenols in organic solvents ha s been studied. Two competing routes have been shown to be followed un der the reaction conditions, i.e. elimination-addition (the sulfene me chanism) and nucleophilic substitution at the sulfonyl group sulfur (p redominantly general-base catalysis). The influence of the substrate, reactant and catalyst structure, as well as the nature of the medium, upon the rate and relationship between the competing routes have been investigated.