The financial support of the NSF (Grant CHE0315275), ONR (Grant N00014-021-0600), and DTRA (HDTRA 1-07-1-0024) is gratefully acknowledged. The Bruker (Siemens) SMART APEX diffraction facility was established at the University of Idaho with the assistance of the NSF-EPSCoR program and the M. J. Murdock Charitable Trust, Vancouver, WA (USA)
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Communication
Activation of the C![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
F Bond: Transformation of CF3N![[DOUBLE BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8fe.gif)
N- into 5-Azidotetrazoles†
Article first published online: 1 AUG 2008
DOI: 10.1002/anie.200802459
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 47, Issue 37, pages 7087–7090, September 1, 2008
Additional Information
How to Cite
Abe, T., Tao, G.-H., Joo, Y.-H., Huang, Y., Twamley, B. and Shreeve, Jean'ne M. (2008), Activation of the CF Bond: Transformation of CF3NN- into 5-Azidotetrazoles. Angew. Chem. Int. Ed., 47: 7087–7090. doi: 10.1002/anie.200802459
- †
Publication History
- Issue published online: 27 AUG 2008
- Article first published online: 1 AUG 2008
- Manuscript Received: 27 MAY 2008
Funded by
- NSF. Grant Number: CHE0315275
- ONR. Grant Number: N00014-021-0600
- DTRA. Grant Number: HDTRA 1-07-1-0024
Keywords:
- azo compounds;
- CF activation;
- hydrazones;
- nitrogen heterocycles;
- tetrazoles
N&Ns: The CF bond of trifluoromethylazoalkanes, in the presence of a hydrogen at the α carbon, is activated under basic conditions to form a difluoromethylene intermediate with a conjugated double bond, which is transformed in good yield to the corresponding 5-azido-(1-dialkylimino)tetrazole by reaction with NaN3.