Low Temperature Free-Radical Reactions Initiated with tert -Butyl p-Benzoylperbenzoate. Selective Acyl Radical Additions to Substituted Olefins

Journal of Organic Chemistry

Volumn 50, Issue 19, 1985, Pages 3498-3502

  Gottschalk, Peter ^a   Neckers, D C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000884797     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00219a015     Document Type: Article

References (13)

1. Julia, M. Acc. Chem. Res. 1971, 4 (11), 386.
2. (a) Beckwith, A. L. J.; Ingold, K. U. In “Rearrangements in Ground and Excited States”; Mayo, P. de, Ed.; Acacemic Press: New York, 1980; Vol. 1, pp 161–310. (b) Beckwith, A. L. J.; Easton, D. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482.
3. Surzur, J. M. In “Reactive Intermediates”; Abramovitch, R. A., Ed.lenum Press: New York, 1982; Vol. 2, Chapter 3.
4. For recent examples, see: Hart, D. J.; Choi, J. K., Tsai, Y.-M. Tetrahedron Lett. 1982, 4765. Hart, D. J.; Chuang, C. P. J. Org. Chem. 1983, 48, 1782.
5. For recent examples, see: Stork, G.; Mook, R., Jr. J. Am. Chem. Soc. 1983,105, 3720. Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 3741. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765.
6. Thijs, L.; Gupta, S. N.; Neckers, D. C. J. Org. Chem. 1979, 44, 4123. (8) Gupta, S. N.; Thijs, L.; Neckers, D. C. J. Poly. Sci. 1981,19, 855.
7. Patrick, T. M., Jr. J. Org. Chem. 1952, 17, 1009.
8. (a) Walling, C. “Free Radicals in Solution”; John Wiley and Sons, Inc.: New York, 1954p 153–154. (b) Huyser, E. S. “Free Radical Chain Reactions”; Wiley Interscience: New York, 1970 152. (c) Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 11,753.
9. Low temperature addition of RC(=0) to olefins can be carried out by direct photolysis (253.7 mm) of RCHO, but the reaction is slow. See: Kharasch, M. S.; Urry, W. H.; Kuderna, B. M. J. Org. Chem. 1949, 3, 248. (12) Reference 10b, pp 153–154.
10. Fraser-Reid, B.; Andeson, R. C.; Hicks, D. R.; Walker, D. L.Can, J. Chem. 1977, 55 (23), 3986.
11. Hart, D. J. Science (Washington, D.C.) 1984, 223, 883. (15) Urry, W. H.; Mullenbach, T. T. U.S. Patent 3957 825, May 18, 1976; Chem. Absts. 1977, 85, 108563.
12. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647.
13. Maercker, A. In “Organic Reactions”; John Wiley and Sons, Inc.: New York, 1965; Vol. 3, p. 270.