Benzylic oxidation by sodium bismuthate in acetic acid: A simple method for the synthesis of polycyclic aromatic ketones

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7247-7250

  Banik, Bimal K ^a   Venkatraman, M S ^a   Mukhopadhyay, Chhanda ^a   Becker, Frederick F ^a  

^a UNIVERSITY OF TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; POLYCYCLIC AROMATIC COMPOUND;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; OXIDATION; SYNTHESIS;

EID: 0032192193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01556-1     Document Type: Article

References (33)

1. 1. ( a ) Burstein, G. T.; Wright, G. A. Nature ( London ), 1969, 221, 169.
2. ( b ) Vogel, A. I. Qualitative Inorganic Analysis, Longman Scientific and Technical: England; Wiley: New York, 1987.
3. 2. Rigby, W. J. Chem. Soc. 1950, 1907; 1951, 793.
4. 2. Rigby, W. J. Chem. Soc. 1950, 1907; 1951, 793.
5. 3. ( a ) Hewgill, F. R.; Kennedy, B. R.; Kilpin, D. J. Chem. Soc. 1965, 2904.
6. ( b ) Hewgill, F. R.; Middleton, B. S. J. Chem. Soc. 1965, 2914.
7. ( c ) Adderly, C. J. R.; Hewgill, F. R. J. Chem. Soc.C. 1968, 2770.
8. ( d ) Adler, E.; Holmberg, K.; Ryrfor, L. O. Acta Chem. Scand. Ser. B, 1974, 28, 888.
9. ( e ) Kon, E.; McNelis, E. J. Org. Chem. 1975, 40, 1515.
10. ( f ) Kon, E.; McNelis, E. J. Org. Chem. 1975, 41, 1646.
11. 4. Truesdale, L. K.; Reuman, M. E. J. Org. Chem. 1980, 45, 726.
12. 5. Floresca, R.; Kurihara, M.; Watt, D.; Demir, A. J. Org. Chem. 1993, 58, 2196.
13. 6. ( a ) Barton, D. H. R.; Finet, J. P. Pure Appl. Chem. 1987, 59, 937.
14. ( b ) Abramovitch, R. A.; Barton, D. H. R.; Finet, J. P. Tetrahedron 1988, 44, 3039.
15. ( c ) Finet, J. P. Chem. Rev. 1989, 89.
16. ( d ) Firouzabadi, H.; Mohammadpour-Baltork, I. Bull. Chem. Soc. Jpn. 1992, 65, 1131.
17. ( e ) Postel, M.; Dunach, E. Coordination Chemistry Rev. 1996, 155, 127.
18. 7. Harvey, R. G., Pataki, J.; Cortez, C.; DiRaddo, P.; Yang, C. J. Org. Chem. 1991, 56, 1210.
19. 8. ( a ) Rathore, R.; Saxena, N.; Chandrasekaran, S. Synth. Commun. 1986, 16, 1493.
20. ( b ) Maurer, J. L.; Berchier, F.; Serino, A. J.; Knobler, C. B.; Hawthrone, M. F. J. Org. Chem. 1990, 55, 838.
21. ( c ) Ghosh, S.; Banik, B. K.; Ghatak, U. R. J. Chem. Soc., Perkin Transl, 1991, 3195.
22. ( d ) Ghosh, A. K.; Ray, C.; Ghatak, R. Tetrahedron Lett. 1992, 33, 655.
23. ( e ) Ghosh. A. K.; Mukhopadhyay; Ghatak, U. R. J. Chem. Soc., Perkin TransI 1994, 327.
24. 9. ( a ) Wenkert, E.; Jackson, B. G. J. Am. Chem. Soc. 1958, 211.
25. ( b ) Ghatak, U. R.; Chatterjee, N. R.; Banerjee, A. K.; Chakravarty, J.; Moore, R. E. J. Org. Chem. 1969, 34, 3739.
26. ( c ) Banik, B. K.; Ghosh, S.; Ghatak, U. R. Tetrahedron, 1988, 44, 6947.
27. ( d ) Banik, B. K.; Ghatak, U. R. Synth. Commun. 1989, 19, 1351.
28. 10. Muzart, J. Tetrahedron Lett. 1987, 28, 2131.
29. 11. Firouzabadi, H.; Salechi, P.; Sardarian, A. R.; Seddighi, M. Synth. Commun. 1991, 21, 1121
30. 12. Harvey, R. G.; Abu-shqara, E.; Yang, C. J. Org. Chem. 1992, 57, 6313.
31. 13. ( a ) Wiberg, K. B.; Evans, R. J. Tetrahedron, 1960, 8, 313.
32. ( b ) Rocek, J. Tetrahedron Lett. 1962, 4, 135.
33. 14. All products have been characterized through a comparison of mp, TLC and NMR with authentic compounds.