Ring opening and ring expansion of 8-cyano-tetrazolo[1,5-alpha]pyridine with secondary amines. Reactions of azides, tetrazoles and nitrenes with nucleophiles, part 2

Addicott, Chris, Bernhardt, Paul V. and Wentrup, Curt (2009) Ring opening and ring expansion of 8-cyano-tetrazolo[1,5-alpha]pyridine with secondary amines. Reactions of azides, tetrazoles and nitrenes with nucleophiles, part 2. ARKIVOC, 2009 vi: 30-37. doi:10.3998/ark.5550190.0010.604


Author Addicott, Chris
Bernhardt, Paul V.
Wentrup, Curt
Title Ring opening and ring expansion of 8-cyano-tetrazolo[1,5-alpha]pyridine with secondary amines. Reactions of azides, tetrazoles and nitrenes with nucleophiles, part 2
Formatted title
Ring opening and ring expansion of 8-cyano-tetrazolo[1,5α]pyridine with secondary amines. Reactions of azides, tetrazoles and nitrenes with nucleophiles, part 2
Journal name ARKIVOC   Check publisher's open access policy
ISSN 1551-7012
1551-7004
Publication date 2009-01-04
Year available 2009
Sub-type Article (original research)
DOI 10.3998/ark.5550190.0010.604
Open Access Status DOI
Volume 2009
Issue vi
Start page 30
End page 37
Total pages 8
Editor Eric Scriven
Place of publication Gainesville, FL, USA
Publisher Arkat USA
Language eng
Subject C1
030503 Organic Chemical Synthesis
970103 Expanding Knowledge in the Chemical Sciences
Abstract 8-Cyanotetrazolo[1,5-a]pyridine 6T undergoes photochemical ring expansion to afford 1,3-diazepine 7 with diisopropylamine, but with stronger nucleophiles such as dimethylamine a rapid, quantitative ring opening reaction affords dienyltetrazoles 8 and 9 in the dark ( an Addition of Nucleophile - Ring Opening reaction).
Formatted abstract
8-Cyanotetrazolo[1,5-α]pyridine 6T undergoes photochemical ring expansion to afford 1,3- diazepine 7 with diisopropylamine, but with stronger nucleophiles such as dimethylamine a rapid, quantitative ring opening reaction affords dienyltetrazoles 8 and 9 in the dark (an Addition of Nucleophile – Ring Opening reaction).
Keyword Pyridine
Tetrazole
Nucleophilic ring opening
1H-1,3-diazepines
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Part (vi): Commemorative Issue in Honor of Prof. Henk van der Plas on the occasion of his 80th anniversary Facilitator: Bert Maes Scientific Editor: Hiriyakkanavar Ila

Document type: Journal Article
Sub-type: Article (original research)
Collections: 2010 Higher Education Research Data Collection
School of Chemistry and Molecular Biosciences
 
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Created: Thu, 03 Sep 2009, 18:03:26 EST by Mr Andrew Martlew on behalf of School of Chemistry & Molecular Biosciences