The Action of Trifluoromethanesulfonic Acid on Naphthalene

Abstract

Trifluoromethanesulfonic ( triflic ) acid reacts with naphthalene at room temperature to give a complex mixture from which five products have been isolated and identified as follows: (E)-3-benzylidene-2,3-dihydro-1H-benz[e]indene (2) (yield 15-20%), 1,2,3,4-tetrahydroanthracene (7) (c. 0.5%), 4-phenyl-1,2-dihydroanthracene (8), 3,4-dihydro-1,2′-binaphthyl (9a′), 4-(2-naphthyl)-1,2-dihydroanthracene (10) [yields of (8), (9a′) and (10) each less than 0.1%]. Also formed is (Z)-2-benzylidene-1,3-dihydro-1H-benz[e]indene (6) which is formed reversibly from (2) by the action of triflic acid. Mechanisms are proposed for the formation of these products.