Radical-mediated cyclisation of ω-aryl-β-dicarbonyl compounds to tetrahydrobenzocyclohepten-6-ones, hexahydrobenzocycloocten-6-ones and naphthalen-2(1H)-ones

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 24, 1997, Pages 3613-3621

  Jamie, Joanne F ^a   Rickards, Rodney W ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748646983     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704869f     Document Type: Article

References (49)

1. J. F. Jamie and R. W. Rickards, J. Chem. Soc., Perkin Trans. 1, 1996, 2603.
2. A. Citterio, L. Pesce, R. Sebastiano and R. Santi, Synthesis, 1990, 142.
3. A. Citterio, D. Fancelli, C. Finzi, L. Pesce and R. Santi, J. Org. Chem., 1989, 54, 2713.
4. I. S. Aidhen and N. S. Narasimhan, Tetrahedron Lett., 1989, 30, 5323;
5. Indian J. Chem., Sect. B. 1993, 32, 222.
6. (a) B. B. Snider, R. Mohan and S. A. Kates, J. Org. Chem., 1985, 50, 3659;
7. (b) B. B. Snider, R. Mohan and S. A. Kates, Tetrahedron Lett., 1987, 28, 841:
8. (c) R. Mohan, S. A. Kates, M. A. Dombroski and B. B. Snider, Tetrahedron Lett., 1987, 28, 845;
9. (d) B. B. Snider and M. A. Dombroski, J. Org. Chem., 1987, 52, 5487;
10. (e) B. B. Snider, J. J. Patricia and S. A. Kates, J. Org. Chem., 1988, 53, 2137;
11. (f) J. E. Merritt, M. Sasson, S. A. Kates and B. B. Snider, Tetrahedron Lett., 1988, 29, 5209;
12. (g) P. Jones and G. Pattenden, Synlett., 1997, 398.
13. J. R. Peterson, R. S. Egler, D. B. Horsley and T. J. Winter, Tetrahedron Lett., 1987, 28, 6109.
14. E. J. Corey and M-c. Kang, J. Am. Chem. Soc., 1984, 106, 5384.
15. G. G. Melikyan, Synthesis, 1993, 833;
16. Org. React., 1997, 49, 427;
17. J. Iqbal, B. Bhatia and N. K. Nayyar, Chem. Rev., 1994, 94, 519;
18. B. B. Snider, Chem. Rev., 1996, 96, 339.
19. J. E. Merritt, M. Sasson, S. A. Kates and B. B. Snider, Tetrahedron Lett., 1988, 29, 5209.
20. B. B. Snider and J. E. Merritt, Tetrahedron, 1991, 47, 8663.
21. F. A. Hochstein and W. G. Brown, J. Am. Chem. Soc., 1948, 70, 3484.
22. D. Seebach, T. Weller, G. Protschuk, A. K. Beck and M. S. Hockstra, Helv. Chim. Acta, 1981, 64, 716.
23. S. Masuda, M. Tanaka and T. Ota, Chem. Lett., 1984, 1327.
24. K. M. Pietrusiewicz and J. Monkiewicz, Tetrahedron Lett., 1986, 27, 739.
25. B. E. Maryanoff, A. B. Reitz, M. S. Mutter, R. R. Inners and H. R. Almond, Jr., J. Am. Chem. Soc., 1985, 107, 1068.
26. J. Fayos, J. Clardy, L. J. Dolby and T. Farnham, J. Org. Chem., 1977, 42, 1349.
27. R. M. Silverstein, G. C. Bassler and T. C. Morrill, Spectrometric Identification of Organic Compounds, 4th edn., Wiley, New York, 1981.
28. Organic Electronic Spectral Data, ed. O. H. Wheeler and L. A. Kaplan, Wiley, New York, 1966, vol. III, p. 81.
29. J. H. Beynon in Mass Spectrometry and its Applications to Organic Chemistry, Elsevier, Amsterdam, 1960, p. 262.
30. F. A. Bovey, in NMR Data Tables for Organic Compounds, Wiley, New York, 1967, vol. 1.
31. P. Sohár, in Nuclear Magnetic Resonance Spectroscopy, CRC Press, Florida, 1984, vol. III, p. 140.
32. L. Friedman and H. Shechter, J. Org. Chem., 1960, 25, 877.
33. P. C. Meltzer, H. C. Dalzell and R. K. Razdan, J. Chem. Soc., Perkin Trans 1, 1981, 2825.
34. B. Lal, P. Singh, A. P. Bhaduri and K. Kar, Indian J. Chem., 1975, 13, 898.
35. M. F. Comber, M. V. Sargent, B. W. Skelton and A. H. White, J. Chem. Soc., Perkin Trans. 1, 1989, 441.
36. M. Kuchar, B. Brunová, V. Rejholec, Z. Roubal and O. Nemecek, Collect. Czech. Chem. Commun., 1976, 41, 633.
37. R. Adams, S. MacKenzie, Jr. and S. Loewe, Jr., J. Am. Chem. Soc., 1948, 70, 664.
38. S. Winstein and R. Heck, J. Am. Chem. Soc., 1956, 78, 4801.
39. A. Bhati, Tetrahedron, 1962, 18, 1519.
40. L. Crombie, W. M. L. Crombie, S. V. Jamieson, P. Tuchinda and A. J. Whitaker, J. Chem Soc., Perkin Trans. 1, 1982, 1485.
41. B. S. Furniss, A. J. Hannaford, P. W. G. Smith and A. R. Tatchell in Vogel's Textbook of Practical Organic Chemistry, Longman Scientific and Technical, London, 5th edn., 1989.
42. C. J. Pouchert, The Aldrich Library of NMR Spectra, Aldrich Chemical Co., USA, 2nd edn., 1983. vol. 2. p. 180.
43. R. F. Nystrom and W. G. Brown, J. Am. Chem. Soc., 1947, 69, 1197.
44. L. H. Klemm, R. A. Klemm, P. S. Santhanam and D. V. White, J. Org. Chem., 1971, 36, 2169.
45. S. Lindenfors, Ark. Kemi, 1958, 12, 267.
46. (a) A. Svendsen and P. M. Boll, Tetrahedron, 1973, 29, 4251;
47. (b) F. Serratosa and E. Sole, An. R. Soc. Esp. Fis. Quim. Ser. B, 1996, 62, 431;
48. Chem. Abstr., 1967, 66, 2623f.
49. K. Omura and D. Swern, Tetrahedron, 1978, 34, 1651.