9-azidoacridine and 9-acridinylnitrene

Taherpour, Avat Arman, Kvaskoff, David, Bernhardt, Paul V. and Wentrup, Curt (2010) 9-azidoacridine and 9-acridinylnitrene. Journal of Physical Organic Chemistry, 23 4: 382-389. doi:10.1002/poc.1657


Author Taherpour, Avat Arman
Kvaskoff, David
Bernhardt, Paul V.
Wentrup, Curt
Title 9-azidoacridine and 9-acridinylnitrene
Journal name Journal of Physical Organic Chemistry   Check publisher's open access policy
ISSN 0894-3230
1099-1395
Publication date 2010-04
Sub-type Article (original research)
DOI 10.1002/poc.1657
Volume 23
Issue 4
Start page 382
End page 389
Total pages 8
Editor Luis Echegoyen
Place of publication Chichester, U.K.
Publisher Wiley.
Collection year 2011
Language eng
Formatted abstract
Matrix photolysis as well as flash vacuum thermolysis (FVT) of 9-azidoacridine affords 9-acridinylnitrene, which is characterized by its IR and ESR spectra and is photochemically inert. FVT above 600 °C yields a mixture of the five isomeric cyanocarbazoles. Microwave-assisted reaction with diethyl- and dipropylamines in solution affords acridinylformamidine and acridinylpropionamidine, respectively. Microwave-assisted reaction with dimethylamine causes nucleophilic displacement of the azido group. Microwave-assisted 1,3-dipolar cycloaddition with phenylacetylene yields the two regioisomeric 9-(4- and 5-phenyl-1,2,3-triazol-1-yl)acridines, whose structures were established by X-ray crystallography.
Copyright © 2010 John Wiley & Sons, Ltd.
Keyword Azides
FVT
Nitrenes
Matrix isolation
Photolysis
Laser flash-photolysis
Ring-expansion
Substituted 9-(1,2,3-triazol-1-YL)acridines
Nitrene rearrangements
Cycloaddition
Carbazoles
Chemistry
Carbenes
Azides
1H-1,3-diazepines
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2011 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Sun, 02 May 2010, 00:04:39 EST