Comments on photochromism of 3-(3-pyridyl)sydnone and 4-alkenylsydnones

Wentrup, Curt; Kvaskoff, David; Veedu, Rakesh N.

doi:10.1016/j.jphotochem.2014.10.010

Cited by 3 publications

(2 citation statements)

References 16 publications

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“…The rearrangement reactions described above are assumed to take place in the singlet nitrenes. Calculations indicate a singlet–triplet gap on the order of 8–9 kcal/mol and low barriers for the rearrangements of the singlet nitrenes. , …”

Section: Azidesmentioning

confidence: 93%

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Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles

2017

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Flash vacuum pyrolysis (FVP) of azides is an extremely valuable method of generating nitrenes and studying their thermal rearrangements. The nitrenes can in many cases be isolated in low-temperature matrices and observed spectroscopically. NH and methyl, alkyl, aralkyl, vinyl, cyano, aryl and N-heteroaryl, acyl, carbamoyl, alkoxycarbonyl, imidoyl, boryl, silyl, phosphonyl, and sulfonyl nitrenes are included. FVP of triazoloazines generates diazomethylazines and azinylcarbenes, which often rearrange to the energetically more stable arylnitrenes. N elimination from monocyclic 1,2,3-triazoles can generate iminocarbenes, 1H-azirines, ketenimines, and cyclization products, and 1,2,4-triazoles are precursors of nitrile ylides. Benzotriazoles are preparatively useful precursors of cyanocyclopentadienes, carbazoles, and aza-analogues. FVP of 5-aryltetrazoles can result in double N elimination with formation of arylcarbenes or of heteroarylcarbenes, which again rearrange to arylnitrenes. Many 5-substituted and 2,5-disubstituted tetrazoles are excellent precursors of nitrile imines (propargylic, allenic, or carbenic), which are isolable at low temperatures in some cases (e.g., aryl- and silylnitrile imines) or rearrange to carbodiimides. 1,5-Disubstituted tetrazoles are precursors of imidoylnitrenes, which also rearrange to carbodiimides or add intramolecularly to aryl substituents to yield indazoles and related compounds. Where relevant for the mechanistic understanding, pyrolysis under flow conditions or in solution or the solid state will be mentioned. Results of photolysis reactions and computational chemistry complementing the FVP results will also be mentioned in several places.

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Section: Azidesmentioning

confidence: 93%

“…Calculations indicate a singlet−triplet gap on the order of 8−9 kcal/mol and low barriers for the rearrangements of the singlet nitrenes. 284,299…”

Section: Imidoyl Azides [Rc(nr′)−n 3 ] and Imidoylnitrenes [R(cnr′)−n]mentioning

confidence: 99%

Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles

2017

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1,2,3-Oxadiazoles

Fraser¹

2022

Comprehensive Heterocyclic Chemistry IV

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Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

Albota

Caira

Drăghici

et al. 2016

Beilstein J. Org. Chem.

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The synthesis of sydnones heteroarylated at C-4 with an indolizine was achieved by Chichibabin (Tschitschibabin) indolizine synthesis starting from the corresponding sydnone-N-pyridinium bromides. The latter compounds were also transformed to sydnone-indolizines connected through a keto group at the C-4 position by refluxing them in 1,2-epoxybutane with an activated alkyne. The structures of the new compounds were assigned by FTIR, NMR spectroscopy and X-ray analysis.

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Comments on photochromism of 3-(3-pyridyl)sydnone and 4-alkenylsydnones

Cited by 3 publications

References 16 publications

Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles

Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles

1,2,3-Oxadiazoles

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

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