Radical-Cation Catalysis in the Synthesis of Diphenylmethanes via the Dealkylative Coupling of Benzylic Ethers

Journal of Organic Chemistry

Volumn 60, Issue 23, 1995, Pages 7479-7490

  Rathore, Rajendra ^a   Kochi, Jay K ^a  

^a UNIVERSITY OF HOUSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000970037     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00128a020     Document Type: Article

References (17)

1. For the mesolytic cleavage of C-C bonds in cation radicals, see: Maslak, P.; Narvaez, J. N. Angew. Chem. 1990, 102, 302.
2. For the facile loss of (benzylic) protons from related radical cations in the first step of eq 17, see: Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 7472.
3. Masnovi, J. M.; Sankararaman, S.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 2263.
4. Fasani, E.; Mella, M.; Albini, A. J. Chem. Soc, Perkin Trans 2 1995, 449.
5. Lewis, F. D.; Petisce, J. R. Tetrahedron 1986, 42, 6207.
6. de Nicholas, A. M. P.; Arnold, D. R. Can. J. Chem. 1982, 60, 2165.
7. Simons, J. H.; Archer, S. J. Am. Chem. Soc. 1940, 62, 1623.
8. McKenna, J. F.; Sowa, F. J. J. Am. Chem. Soc. 1937, 59, 470 and references therein.
9. Gassman, P. G.; Singleton, D. A. J. Am. Chem. Soc. 1984, 106, 7993.
10. Yueh, W.; Bauld, N. L. J. Chem. Soc, Perkin Trans 2 1995, 871.
11. Ciminale, F.; Lopez, L.; Mele, G. Tetrahedron 1994, 50, 12685.
12. Lopez, L.; Troisi, L. Tetrahedron Lett. 1989, 30, 3097.
13. Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, P. A., Jr.; Reynolds, D. W.; Wirth, D. D.; Chiou, H. S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371.
14. Chanon, M. Bull. Soc. Chim. Fr. 1985, 209.
15. Bockman, T. M.; Kochi, J. K. J. Phys. Org. Chem. 1994, 7, 325.
16. Staab, H. A.; Haffner, H. Chem. Ber. 1977, 110, 3358.
17. Schill, G. Justus Liebigs Ann. Chem. 1966, 691, 79.