Nitrile ylides: allenic and propargylic structures from pyrazinylnitrenes. Experimental and theoretical characterization

Begue, Didier, Addicott, Chris, Burgard, Riko, Bednarek, Pawel, Guille, Emilie, Baraille, Isabelle and Wentrup, Curt (2014) Nitrile ylides: allenic and propargylic structures from pyrazinylnitrenes. Experimental and theoretical characterization. Journal of Organic Chemistry, 79 5: 2148-2155. doi:10.1021/jo500002r

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Author Begue, Didier
Addicott, Chris
Burgard, Riko
Bednarek, Pawel
Guille, Emilie
Baraille, Isabelle
Wentrup, Curt
Title Nitrile ylides: allenic and propargylic structures from pyrazinylnitrenes. Experimental and theoretical characterization
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
1520-6904
Publication date 2014-03-07
Year available 2014
Sub-type Article (original research)
DOI 10.1021/jo500002r
Open Access Status File (Author Post-print)
Volume 79
Issue 5
Start page 2148
End page 2155
Total pages 8
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Formatted abstract
Matrix photolysis of 2-pyrazinyl azides/tetrazolo[1,5-a]pyrazines generates nitrile ylides 15 via pyrazinylnitrenes 13 and triazacycloheptatetraenes 14. The nitrile ylides 15 are characterized by IR spectroscopy in conjunction with harmonic and anharmonic vibrational frequency calculations. The nitrile ylides exist in the matrices in the Z,Z-conformations in which they are born. Substitution on the nitrile carbon of nitrile ylides has a profound effect on their structure. Even different conformers of the same molecule can have differences up to 200 cm–1 in the IR absorptions of the ylide moieties. Nitrile ylides 15a and 15b (R = H or Cl, R′ = H) have allenic structures (15 Allenic). Nitrile ylide 15c (R = R′ = CH3) has a distinctly propargylic structure (15 Propargylic) in the experimentally observed Z,Z-conformation.
Keyword Nitrile ylides
Pyrazinylnitrenes
Allenic and propargylic structures
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
School of Chemistry and Molecular Biosciences
 
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