Trapping of cyclopropenyl radicals by 5,5-dimethyl-1-pyrroline-N-oxide

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5096-5099

  Cano, Montserrat ^a   Quintana, Jordi ^a   Juliá, Luís ^a   Camps, Francisco ^a   Joglar, Jesús ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; RADICAL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DECARBOXYLATION; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; HYDROGEN BOND; NONHUMAN; PHOTOLYSIS;

EID: 0033002248     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9900026     Document Type: Article

References (13)

1. Cano, M.; Fabriàs, G.; Camps, F.; Joglar, J. Tetrahedron Lett. 1998, 39, 1079-1082.
2. (a) Schreiner, K.; Berndt, A. Angew. Chem., Int. Ed. Engl. 1976, 15, 698.
3. (b) Closs, G. L., Evanochko, W. T.; Norris, J. R. J. Am. Chem. Soc. 1982, 104, 350-352.
4. (c) Sutcliffe, R.; Lindsay, D. A.; Griller, D.; Walton, J. C.; Ingold, K. U. J. Am. Chem. Soc. 1982, 104, 4674-4676.
5. (d) Closs, G. L.; Redwine, O. D. J. Am. Chem. Soc. 1986, 108, 506-507.
6. Compound 1b has been prepared as described in Okada, K; Okamoto, K.; Oda, M. J. Am. Chem. Soc. 1988, 110, 8736-8738 starting from the corresponding 2,3-diphenyl-2-cyclopropenecarboxylic acid (see Experimental Section).
7. γ-H = 1.97 G). Owing to the strong interference of this adduct, it was very difficult to detect any other contribution from cyclopropenyl spin adducts.
8. We tried to test nickel peroxide to remove hydrogen from cyclopropenes in the presence of either DMPO or 2-methyl-2-nitroso-propane as spin traps. However, the blank experiments gave complex spectra that made this procedure useless.
9. Compounds 3a-e have been synthesized according to the methodology described in: Quintana, J.; Barrot, M.; Fabriàs, G.; Camps, F. Tetrahedron 1998, 54, 10187-10198 and references therein. Diphenylcyclopropene 3f was prepared as reported in: Yoshida, Z.; Miyahara, H. Chem. Lett. 1972, 335-338 (see Experimental Section).
10. Compounds 3a-e have been synthesized according to the methodology described in: Quintana, J.; Barrot, M.; Fabriàs, G.; Camps, F. Tetrahedron 1998, 54, 10187-10198 and references therein. Diphenylcyclopropene 3f was prepared as reported in: Yoshida, Z.; Miyahara, H. Chem. Lett. 1972, 335-338 (see Experimental Section).
11. (a) Janzen, E. G.; I-Ping Liu, J. J. Magn. Reson., 1973, 9, 510-512.
12. (b) Janzen, E. G.; Anderson Evans, C.; I-Ping Liu, J. J. Magn. Reson. 1973, 9, 513-516.
13. •(=O) type. The presence of this artifact could be due to decomposition of the sample under the EPR experimental conditions.