Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 5, Pages 2148-2155Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo500002r
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- Australian Research Council
- University of Queensland
- Australian Government (MAS) [g01]
- Aventis-Foundation
- Deutsche Akademische Austausch-dienst (DAAD)
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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. Nitrite 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.
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