Photolysis of 2-methyl-5-phenyltetrazole

Fraser, Robert R.; Gurudata,; Haque, K. E.

doi:10.1021/jo01264a077

Cited by 21 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…uber Photoreaktionen von 1,3-Diazabicyclo-[3,1,O]hex-3-enen, die intermediar zu Zwitterionen des Typs 12 fiihren, wurde kiirzlich berichtet [9] [lo]. Ganz analog laisst sich auch das Auftreten von 2,4,5-Triaryl-l,2,3-triazolen bei der Photolyse von 3,4-Diaryl-sydnonen [l] [6] und 2,5-Diaryl-[6] und 2-Methyl-5-aryltetrazolen [12] erklaren, wenn man annimmt, dass die intermediar auftretenden …”

Section: )unclassified

Zur Photodimerisierung von 3‐Phenyl‐2H‐azirinen. Vorläufige Mitteilung

Gakis

Märky

Hansen

et al. 1972

Helvetica Chimica Acta

View full text Add to dashboard Cite

the case of 1,3-diaryl-lH-diazirines which are intermediates in the photolysis of 3,4diarylsydnones [loj.Photolysis of 4 yielded 4-phenyl-3-phenyliniino-l-azabicyclo[2,1,0]pentane 1101, whereas 2,4,5-triphenyl-imidazole Summary. Irradiation of 3-phenyl-2H-azirine (2) in benzene solution with a high-pressure inercury lamp yields 4,5-diphenyl-l, 3-diazabicyclo[3,1,0]hex-3-ene (4) and not 3-phenylimino-4phenyl-l-azabicyclo[2,l,0]pentane (11, as had been reported previously by others [ 2 ] . 2-Methyl-3phenyl-2 H-azirine (3) yields on irradiation a 2 :1 mixture of 2-exo, 6-exo-and 2-endo, 6-exo-dimethyl-4,S-diphcnyl-l, 3-diazabicyclo[3,1,0]hex-3-ene (2-exo, 6-exo-and 2-endo, 6-exo-5). Irradiation of 2,3-diphenyl-2 H-azirine (8) leads t o thc formation of 2,4,5-triphenyl-imidazole (9) and tetraphenylpyrazine (10). The suggested reaction path for the generation of 9 and 10 is shown in Scheme 2 .Kurzlich wurde mitgeteilt [ 21, dass bei der Bestrahlung von a-Azidostyrol in benzolischer Losung init einer Quecksilber-Hochdrucklampe neben 3-Phenyl-2H-azirin (2) (vgl. auch 131) in 10% Ausbeute ein weiteres, kristallines Photoprodukt (Snip. 137-140') isoliert werden konnte, dem auf Grund seiner spektralen Daten (NMR .-, 1) 2) 18. Mitteilung uber Photoreaktionen; 17. Mitteilung: siehe [l]. Eine ausfuhrliche Mitteilung sol1 in dieser Zeitschrift erscheinen

show abstract

Section: )unclassified

Zur Photodimerisierung von 3‐Phenyl‐2H‐azirinen. Vorläufige Mitteilung

Gakis

Märky

Hansen

et al. 1972

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…The various methods used for generation of nitrilimines include: 1. Thermal [11][12][13] and photochemical [14][15][16][17] extrusion of nitrogen from tetrazoles.…”

Section: R-c R-cmentioning

confidence: 99%

Tandem in situ generation and 1,5-electrocyclization of N-hetaryl nitrilimines. A facile methodology for synthesis of annulated 1,2,4-triazoles and their acyclo C-nucleosides

Shawali¹

2009

Arkivoc

View full text Add to dashboard Cite

show abstract

“…According to Padwa and Smolanoff 29 , regiospecific additions, which occur in the samesense as the additions to aldehydes, were also obtained on irradiation of 3-phenyl-and 2,3-diphenyl-2H-azirines (43 The photoreaction of 46 and methyl methacrylate also proceeds in the same sense regiospecifically, to give a stereo-isomeric mixture of the pyrroline 52. On the other band, the last-mentioned dipolarophile gives a 2:3-mixture of both pyrroline isomers 53 and 54 on reaction with 3-phenyl-2H-azirine (43), the reaction being no Ionger regiospecific 29 • Since a mixture of 46, a dipolarophile, and xanthone gives no photoproduct under conditions in which the latter absorbs alllight, it can be concluded that the photoreaction with 313 nm light proceeds via the singlet state of 46 29 .…”

mentioning

confidence: 93%