Organoboranes for synthesis: Reaction of organoboranes with representative organic azides. A general stereospecific synthesis of secondary amines and N- …
HC Brown, MM Midland, AB Levy, HC Brown…
Index: Brown, Herbert C.; Midland, M. Mark; Levy, Alan B. Tetrahedron, 1987 , vol. 43, # 18 p. 4079 - 4088
Full Text: HTML
Citation Number: 53
Abstract
Reaction of trialkylboranes with organic azides in refluxing xylene, followed by hydrolysis, leads to good yields of secondary amines. This reaction is highly dependent on the steric effects around both boron and the azide moiety. The reaction becomes much slower when the steric bulk of one of the reagents is increased and fails when both are hindered. The dialkylchloroboranes are more reactive than trialkylboranes and provide better yields of ...
Related Articles:
[Tsukada, Naofumi; Ohnishi, Nozomi; Aono, Shiori; Takahashi, Fusako Organometallics, 2012 , vol. 31, # 21 p. 7336 - 7338]
[Shen, Qilong; Ogata, Tokutaro; Hartwig, John F. Journal of the American Chemical Society, 2008 , vol. 130, # 20 p. 6586 - 6596]
[Sreedhar, Bojja; Venkanna, Gopaladasu T.; Shiva Kumar, Kota Balaji; Balasubrahmanyam, Vura Synthesis, 2008 , # 5 p. 795 - 799]
A General Ruthenium??Catalyzed Synthesis of Aromatic Amines
[Hollmann, Dirk; Baehn, Sebastian; Tillack, Annegret; Beller, Matthias Angewandte Chemie - International Edition, 2007 , vol. 46, # 43 p. 8291 - 8294]
Preparation of N-arylamines from 2-oxo-7-azobicyclo [4.1. 0] heptanes
[Barros, M. Teresa; Dey, Suvendu S.; Maycock, Christopher D.; Rodrigues, Paula Tetrahedron, 2012 , vol. 68, # 31 p. 6263 - 6268]