5//-Dibenz azepine-5-carbonyl, bromination

Furthermore, in the addition of bromine to 44 (in 1,2-dichloroethane, chloroform or carbon tetrachloride, see Scheme 19) to obtain the trans dibromo derivative99 (47), which is found to be in two main conformers100, the formation of the bromonium ion (46) from 5//-dibenz[ >,/]azepine-5-carbonyl chloride (44) is a reversible step. The formation of the bromonium ion (46) follows the association of reagents in the CT complex (45). 49 reacts with hydrogen bromide through the protonated 48, forming" both the dibromo derivative 47 and the olefin 44. The bromonium ion (46) is the probable intermediate... 

Calculations by the Pariser-Parr-Pople method on the quinoneimine obtained by Fremy s salt oxidation of dibenz[6,/]azepine indicate that the carbon adjacent to the carbonyl group is the most nucleophilic center. This is confirmed by nitration [Cu(N03)2-Ac0H] and bromination [NBS-(PhC0)202] studies, in which the 1-substituted derivatives are obtained. However, acylation by Vilsmeier or Friedel-Crafts reaction fails, extensive decomposition of the ring system taking place. 

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