Syntheses and chemistry of some dibenz[c,e]azepines

• Published in: Journal of organic chemistry Vol. 52; no. 4; pp. 529 - 536
• Main Authors: Weitzberg, Moshe, Abu-Shakra, Elias, Azeb, Abdullatif, Aizenshtat, Zeev, Blum, Jochanan
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.02.1987; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Organic compounds; Physical Sciences; Physics; Preparations and properties; Science & Technology; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Reactivity; Molecular structure; Nitrogen heterocycle; Acetalization; Aromatic compound; Tricyclic compound; Experimental study; X ray diffraction; Organic compounds; Crystalline structure
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo00380a010

5-Methyl-,5,7-dimethyl-, and 5,7-diphenyl-substituted and unsubstituted 5H-dibenz[c,e]azepines were prepared by two general routes from [1,1''-biphenyl]-2,2''-dicarboxaldehyde. The unsubstituted dibenzazepine was converted into la,9b-dihydrophenanthro[9,10-b]azirine both by lithium diisopropylamide (LDA) and by UV irradiation. The disubstituted azepine derivatives failed, however, to undergo valence isomerization under such conditions. N-Benzylphenanthrene 9,10-imine was obtained directly from 2''-(bromomethyl)[1,1''-biphenyl]-2-carboxaldehyde and excess benzylamine. Aerial oxidation of 5,7-diphenyldibenz[c,e]azepine in the presence of 50% aqueous NaOH led, under phase-transfer conditions, to 5,7-diphenyldibenz[c,e]azepin-5-ol. Special structural features of this carbinol found by X-ray analysis are discussed.