Evidence for azidyl radical initiated olefin isomerization. One-way isomerization of (Z)-Urocanic acid

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8435-8438

  Kpissay, Armah ^a   Kuhl, C Nicole ^a   Mohammad, Taj ^a   Haber, Ken ^a   Morrison, Harry ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; UROCANIC ACID;

ARTICLE; DRUG SYNTHESIS; ISOMERISM; PHOTOOXIDATION;

EID: 0030696890     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10273-8     Document Type: Article

References (10)

1. Organic Photochemistry. Part 114. Part 113. Agyin, J.K.; Timberlake, L; Morrison, H., J. Am. Chem. Soc., 1997, 119, 7945-7953.
2. Norval, M.; Gibbs, N. K.; Golmour, J., Photochem. Photobiol. 1995, 62, 209-217.
3. Morrison, H.; Deibel, R. M. Photochem. Photobiol. 1986, 43, 663-665.
4. Mohammad, T.; Kasper, A.; Morrison, H. Tetrahedron Lett. 1994, 35, 4903-4906.
5. (a) Workentin, M. S.; Wagner, B. D.; Lusztyk, J.; Wayner, D. D. M. J. Am. Chem. Soc. 1995, 117, 119-126;
6. (b) Workentin, M. S.; Wagner, B. D.; Negri, F.; Zgierski, M. Z.; Lusztyk, J.; Siebrand, W.; Wayner, D. D. M. J. Phys. Chem. 1995, 99, 94-101.
7. Griesbeck, A. G.; Hundertmark, T.; Steinwascher, J. Tetrahedron Lett. 1996, 37, 8367-8370.
8. Here UA is shown in non-ionized form for simplicity but, depending upon the pH of the medium, it can exist in dissociated form.
9. Morrison, H.; Avnir, D.; Bernasconi, C.; Fagan, G. Photochem. Photobiol. 1980, 32, 711-714.
10. We presume that 1 decomposes solely to (E)-UA because of the greater thermodynamic stability anticipated for this isomer, see for example, Chatgilialoglu, C.; Ballestri, M.; Ferreri, C.; Vecchi, D. J. Org. Chem. 1995, 60, 3826-3831.