HALOGENATION REGIOSELECTIVE EN SERIE AROMATIQUE-I CHLORATION DES PHENOLS ET LEURS ETHERS A L'AIDE DE REACTIFS METTANT EN JEU DES INTERACTIONS DONNEUR-ACCEPTEUR

Article abstract of DOI:10.1016/0040-4020(82)87011-7

An efficient regiospecific route for the chlorination of phenol involving hexachlorohexadienones is described.The selectivity is attained by using a reagent tailored in such a way that it is able to participate in charge transfer interactions and hydrogen bonding with the substrate.This recognition between substrate (phenol) and 2,3,4,4,5,6-hexachlorocyclohexa 2,5-dien 1-one 1 which we called "reactif p" allows the chlorination of phenol in the para position.The use of 2,3,4,5,6,6-hexachlorocyclohexa 2,4-dien-1 one 2 we have called "reactif o" permits the chlorination in the ortho position.These two reagents are stable and inexpensive materials, synthetized from pentachlorophenol and chlorine.The chlorination of anisole with these two reagents, gives solely the parachloro derivative, under steric control.