NEW SYNTHETIC ROUTE TO ,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5,10-IMINES THROUGH PHOTOAMINATION OF 5-ALKOXY-5H-DIBENZO[A,D]CYCLOHEPTENES AND 5-HYDROXY-5H-DIBENZO[A,D]CYCLOHEPTENES FOLLOWED BY A TRANSANNULAR REACTION WITH ACETIC-ACID

The photoadditions of ammonia and alkylamines (RNH(2)) to 5-hydroxy- a nd 5-alkoxy-5H-dibenzo[a, d] cycloheptene derivatives (2) occurred at the C10-C11 double bond upon the irradiation of 2 with RNH(2) in the p resence of p-dicyanobenzene. The resulting 5-substituted 10-alkylamino -10,11-dihydro-5H-dibenzo[a, d]cycloheptenes were converted to 5-subst ituted N-alkyl-10,11-dihydro-5H-dibenzo[a, d]cyclohepten-5,10-imines b y a treatment with AcOH.