title: Novel 2,4-methanoadamantane-benzazepine by domino photochemistry of N-(1-adamantyl)phthalimide.
abstract: The photochemical reaction of N-(1-adamantyl)phthalimide (1) gives cleanly one product, the novel hexacyclic benzazepine derivative of 2,4-methanoadamantane 2. Its structure was characterized by spectroscopic methods and X-ray analysis and represent the first example of the 2-azahexacyclo[8.7.1.1 (1,4).0 (4,9).0 (11,16).0 (12,18)]nonadeca-4,6,8-triene skeleton. The product is formed by a domino process of two consecutive excited-state intramolecular gamma-hydrogen-transfer reactions. Base hydrolysis of the benzazepine 2 gives in high yield the keto derivative of the 1,2-substituted adamantane epsilon-amino acid 3.
authors: Department of Organic Chemistry and Biochemistry, Ruder Bosković Institute, 10 000 Zagreb, Croatia. nbasaric@irb.hr
authors: Nikola
authors: N
authors: Basarić
authors: Margareta
authors: M
authors: Horvat
authors: Kata
authors: K
authors: Mlinarić-Majerski
authors: Elmar
authors: E
authors: Zimmermann
authors: Jörg
authors: J
authors: Neudörfl
authors: Axel G
authors: AG
authors: Griesbeck
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D001552:Benzazepines / Q000737:chemistry*; D006868:Hydrolysis; D010777:Photochemistry; D010797:Phthalimides / Q000737:chemistry*
chemical_list: C532595:2,4-methanoadamantane-benzazepine; D000596:Amino Acids; D001552:Benzazepines; D010797:Phthalimides; D000218:Adamantane