Photochemical vinylcyclopropane rearrangements of 1-substituted-3-(2,2- diphenylvinyl)-2,2-dimethylcyclopropanes to cyclopentenes and different heterocycles

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 1056-1060

  Armesto, Diego ^a   Ortiz, Maria J ^a   Agarrabeitia, Antonia R ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPENTENE DERIVATIVE; UNCLASSIFIED DRUG; VINYLCYCLOPROPANE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; IRRADIATION; PHOTOCHEMISTRY;

EID: 0033525052     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981965s     Document Type: Article

References (14)

1. Goldschmidt, Z.; Crammer, B. Chem. Soc. Rev. 1988, 17, 229, and references cited herein.
2. (a) Sasaki, T.; Eguchi, S.; Ohno, M. J. Org. Chem. 1968, 33, 676.
3. (b) Sasaki, T.; Eguchi, S.; Ohno, M. J. Org. Chem. 1970, 35, 790.
4. (c) Ueda, K.; Matsui, M. Tetrahedron 1971, 27, 2771.
5. (d) Ruzo, L. O.; Holmstead, R. L.; Casida, J. E. Tetrahedron Lett. 1976, 35, 3045.
6. (e) Ruzo, L. O.; Casida, J. E. J. Chem. Soc., Perkin Trans. 1 1980, 728.
7. Zimmerman, H. E.; Armesto, D.; Amezua, M. G.; Gannett, T. P.; Johnson, R. P. J. Am. Chem. Soc. 1979, 101, 6367.
8. 1H NMR spectra of the oily residue obtained shows the presence of addition product.
9. (b) Sargent, M. V.; Dean, F. M. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4, p 653.
10. (a) The identity of 12 was established by comparison of its spectroscopic data with those reported (ref 5b) for similar 1,2-oxazines obtained in the DCA-sensitized irradiation of γ,δ-unsaturated oximes.
11. (b) Armesto, D.; Austin, M. K.; Griffiths, O. J.; Horspool, W. M.; Carpintero, M. J. Chem. Soc., Chem. Commun. 1996, 2715.
12. Yields have not been optimized.
13. This aldehyde undergoes spontaneous oxidation in the presence of atmospheric oxygen. The combustion analysis quoted herein corresponds to the carboxylic acid resulting from the oxidation of the aldehyde.
14. Zimmerman, H. E.; Khun, R. T. Tetrahedron 1878, 34, 1775.