Sequential and regioselective Friedel-Crafts reactions of gem-dihalocyclopropanecarbonyl chlorides with benzenes for the synthesis of 4-aryl-1-naphthol derivatives

Article abstract of DOI:10.1016/0040-4039(95)01866-G

Two types of novel, sequential and regioselective Friedel-Crafts reactions of gem-dihalocyclopropanecarbonyl chlorides with benzenes proceeded in a one-pot manner; E-3-aryl-2,2-dihalo-cyclopropanecarbonyl chlorides reacted with substituted benzenes to afford 4-aryl-3-halo-1-naphthols, while 2,2-dichlorocyclopropanecarbonyl chlorides were transformed into 4-aryl-1-naphthols in benzene or p-xylene. Both annulations involved alternative and highly regioselective cyclopropane ring-openings.