Premium
Bromination and Iodination of 6 H ,12 H ‐5,11‐Methanodibenzo[ b , f ][1,5]diazocine: A Convenient Entry to Unsymmetrical Analogs of Tröger's Base
Author(s) -
Didier Delphine,
Sergeyev Sergey
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700253
Subject(s) - halogenation , chemistry , iodine monochloride , aniline , electrophile , paraformaldehyde , base (topology) , medicinal chemistry , derivative (finance) , stereochemistry , combinatorial chemistry , iodine , organic chemistry , catalysis , mathematics , mathematical analysis , financial economics , economics
6 H ,12 H ‐5,11‐Methanodibenzo[ b , f ][1,5]diazocine can easily be prepared from aniline and paraformaldehyde. Its reactions with either N ‐bromosuccinimide (NBS) or with iodine monochloride (ICl) in the presence of a suitable activator smoothly afford 2‐bromo‐ and 2‐iodo‐ derivatives, respectively. The combination of these halogenation methods provides access to the 8‐bromo‐2‐iodo derivative, which is an interesting and otherwise inaccessible intermediate for the synthesis of unsymmetrical analogs of Tröger's base. The reported halogenations represent the first examples of electrophilic substitution in 6 H ,12 H ‐5,11‐methanodibenzo[ b , f ][1,5]diazocine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)