Facile autoxidation of 2-(4-hydroxyphenyl)-3,3-dimethylmethylenecyclopropane. The radical stabilizing ability of the phenoxide group

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1615-1618

  Creary, Xavier ^a   Wolf, Allison ^a   Miller, Kevin ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038615135     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9902576     Document Type: Article

References (10)

1. Creary, X.; Engel, P. S.; Kavaluskas, N.; Pan, L.; Wolf, A. J. Org. Chem. 1999, 64, 5634-5643.
2. Creary, X.; Mehrsheikh-Mohammadi, M. E.; McDonald, S. J. Org. Chem. 1987, 52, 3254-3263.
3. Adam, W.; Harrer, H. M.; Kita, F.; Korth, H.-G.; Nau, W. M. J. Org. Chem. 1997, 62, 1419-1426.
4. Olofson, R. A.; Dougherty, C. M. J. Am. Chem. Soc. 1973, 95, 582-584.
5. Creary, X. J. Org. Chem. 1978, 43, 1777-1783.
6. Formation of a dioxolane by reaction of singlet oxygen with tetranisylcyclopropane has been reported. See: Akasaka, T.; Fukuoka, K.; Ando, W. Tetrahedron Lett. 1991, 32, 7695-76.
7. 2 to cyclopropanes to form dioxolanes has also been reported. See: Schaap, A. P.; Siddiqui, S.; Prasad, G.; Palomino, E.; Lopwz, L. J. Photochem. 1984, 25, 167-181.
8. Creary, X.; Mehrsheikh-Mohammadi, M. E.; McDonald, S. J. Org. Chem. 1989, 54, 2904-2910.
9. For a discussion, see: Hirota, N. In Radical Ions; Kaiser, E. T., Kevan, L., Eds.; Interscience: New York, 1968; pp 35-85.
10. Frisch, M, J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.3, Gaussian, Inc., Pittsburgh, PA, 1995.