SYNTHESIS OF AROMATIC AMINES, AROMATIC ALCOHOLS AND AROMATIC THIOLS BY AROMATIC NUCLEOPHILIC SUBSTITUTION REACTION

摘要

PURPOSE:To synthesize the title compound by converting an aromatic compound once into a compound replaced with phenol, etc., and further replacing the phenol, etc., at the 2-position, with an electrophilic group such as (thio)carbonyl group and then reacting the replaced compound with a nucleophilic agent, when NH2, OH and SH group is introduced into an aromatic ring. CONSTITUTION:A compound expressed by formula I [Q1 is aromatic ring- forming group; EWG is a group having positive valve in deltaP value of Hammett; (m) is 1-5; X is a group expressed by formula II (R4 is H, aryl or alkyl; Q2 is aromatic ring-forming group; Z1 and Z2 are O or S); (n) is 1-3] is subjected to a reaction with a nucleophilic agent expressed by formula III (M is H, metal atom or ammonium; Y is NHR1, OR1 or SR1; R1 is H, alkyl, aryl, etc.) to provide the title substance. The nucleophilic agent is added to Z2 of the group expressed by formula II and then an electron pair is added to the position carrying aromatic nucleophilic substitution to afford Meisenheimer complex intermediate of six membered ring, which is then decomposed to provide the objective product.