Nucleophilicities of Selected Ions in Water at 195 deg C

Article abstract of DOI:10.1021/jo00075a035

The reaction of a benzyl aryl ether (3) with selected ions was studied to determine relative nucleophilicities at 195 deg C in water.Nucleophilic displacement by the ions ocurred at the benzyl carbon to liberate a phenolic group.The primary products of the displacement were independently synthesized and reacted in alkali to determine their stability.Hydrosulfide ion was 20 times more reactive than hydroxide ion with this substrate, while anthrahydroquinone ion was 17 times more reactive.