The metal-ammonia reduction of mono- and dinaphthylbenzenes

摘要: The metal-ammonia reduction of 1- and 2-phenylnaphthalene (9 10, respectively), 1,3-bis(1-naphthyl)benzene (5), 1,3-bis(2-naphthyl)benzene (6), 1,4-bis(1-naphthyl)benzene (7), m-quinquephenyl (8) has been investigated. 9 affords a mixture isomeric dihydro products together with 1-phenyl-1,2,3,4-tetrahydronaphthalene, the effect metal, temperature, quenching methods on product distribution is reported. 10 provided only single (1,4-) isomer plus tetrahydro product. Both 5 7 number dihydro, tetrahydro, hexahydro, octahydro products. On other hand, 6 afforded high yields lithium, exclusively an when 5-7 mol sodium was used. In contrast to terphenyls, which seem have propensity for inner-ring reduction, none naphthyl benzenes showed any tendency reduce in central benzene ring. m-Quinquephenyl reduced two rings no evidence or outer rings.