Heterocyclic analogs of pleiadiene

1-Methylperimidine adds phenylsodium and phenyllithium to the C=N bond to give 1-methyl-2-phenyl-2, 3-dihydroperimidines. However, if benzophenone is present in the reaction mixture, a mixture of 1-methyl-2-phenylperimidine and l-methyl-2, 4-diphenylperimidine (when phenylsodium is used) or l-methyl-2-phenyl-4-(α-hydroxybenzhydryl)perimidine (when phenyllithium is used) is formed. It is assumed that the formation of products involving substitution in the naphthalene ring is associated with the participation of C6H5 and (C6H5)2C-O− radical particles that are formed on reaction of the phenylmetallic compound with benzophenone.