Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers: Dependence of the regioselectivity on alcohol addition and pressure effects

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 1999, Pages 863-869

  Ackermann, Lutz ^a   Heidbreder, Andreas ^b,d   Wurche, Frank ^c   Klärner, Frank Gerrit ^c   Mattay, Jochen ^a,e  

^a UNIVERSITY OF KIEL   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

^c UNIVERSITY OF DUISBURG ESSEN   (Germany)

^d HENKEL KGAA   (Germany)

^e BIELEFELD UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002892691     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807683i     Document Type: Article

References (44)

1. S. Hintz, A. Heidbreder and J. Mattay, Top. Curr. Chem., 1996, 177, 77.
2. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734.
3. L. A. J. Beckwith, Tetrahedron, 1981, 37, 3073.
4. Q. X. Guo, X. Z. Qin, J. T. Wang and F. Williams, J. Am. Chem. Soc., 1988, 110, 1974.
5. C. M. Hudson, M. R. Marzabadi, K. D. Möller and D. G. New, J. Am. Chem. Soc., 1991, 113, 7372.
6. C. M. Hudson and K. D. Möller, J. Am. Chem. Soc., 1994, 116, 3347.
7. T. Shono, I. Nishiguchi, S. Kashimura and M. Okawa, Bull. Chem. Soc. Jpn., 1978, 51, 2181.
8. (a) B. B. Snider and T. Kwon, J. Org. Chem., 1990, 55, 4786;
9. (b) B. B. Snider and T. Kwon, J. Org. Chem., 1992, 57, 2399.
10. (a) J. Mattay, Angew. Chem., Int. Ed Engl., 1987, 26, 825;
11. (b) J. Mattay and M. Vondenhof, Top. Curr. Chem., 1991, 159, 219.
12. (a) A. Heidbreder and J. Mattay, Tetrahedron Lett., 1992, 33, 1973;
13. (b) A. Heidbreder and J. Mattay, J. Inf. Rec. Mater., 1994, 21, 575;
14. (c) A. Heidbreder, PhD Thesis, University of Münster, 1994.
15. M. Chanon and L. Eberson, in Photoinduced Electron Transfer, ed. M. A. Fox and M. Chanon, Elsevier, Amsterdam, 1988, part A, p. 4.
16. S. Hintz, R. Fröhlich and J. Mattay, Tetrahedron Lett., 1996, 37, 7349.
17. (a) S. Hintz, J. Mattay, R. van Eldik and W-F. Fu, Eur. J. Org. Chem., 1998, 1583;
18. (b) S. Hintz, PhD Thesis, University of Münster, 1997.
19. D. P. Curran and C. T. Chang, J. Org. Chem., 1989, 54, 3140.
20. B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986, p. 146.
21. Monographs: (a) N. S. Isaacs, Liquid Phase High Pressure Chemistry, John Wiley, Chichester, 1981; (b) W. J. le Noble, (ed.), Organic High Pressure Chemistry, Elsevier, Amsterdam, 1988; (c) K. Matsumoto and R. Morrin Acheson, (eds.) Organic Synthesis at High Pressure, John Wiley, New York, 1991; (d) W. B. Holzapfel and N. S. Isaacs, (eds.) High-Pressure Techniques in Chemistry and Physics, a Practical Approach, Oxford University Press, Oxford, 1997; (e) R. van Eldik and C. D. Hubbard, (eds.) Chemistry under Extreme or Non-Classical Conditions, Wiley, New York, Spektrum, Heidelberg, 1997; (f) F-G. Klärner and M. K. Diedrich, The effect of pressure on reactions of dienes and polyenes, Chapter II in The chemistry of functional groups, the chemistry of dienes and polyenes, S. Patai and Z. Rappoport, (eds.), vol. 1, Wiley, New York, 1997.
22. Monographs: (a) N. S. Isaacs, Liquid Phase High Pressure Chemistry, John Wiley, Chichester, 1981; (b) W. J. le Noble, (ed.), Organic High Pressure Chemistry, Elsevier, Amsterdam, 1988; (c) K. Matsumoto and R. Morrin Acheson, (eds.) Organic Synthesis at High Pressure, John Wiley, New York, 1991; (d) W. B. Holzapfel and N. S. Isaacs, (eds.) High-Pressure Techniques in Chemistry and Physics, a Practical Approach, Oxford University Press, Oxford, 1997; (e) R. van Eldik and C. D. Hubbard, (eds.) Chemistry under Extreme or Non-Classical Conditions, Wiley, New York, Spektrum, Heidelberg, 1997; (f) F-G. Klärner and M. K. Diedrich, The effect of pressure on reactions of dienes and polyenes, Chapter II in The chemistry of functional groups, the chemistry of dienes and polyenes, S. Patai and Z. Rappoport, (eds.), vol. 1, Wiley, New York, 1997.
23. Monographs: (a) N. S. Isaacs, Liquid Phase High Pressure Chemistry, John Wiley, Chichester, 1981; (b) W. J. le Noble, (ed.), Organic High Pressure Chemistry, Elsevier, Amsterdam, 1988; (c) K. Matsumoto and R. Morrin Acheson, (eds.) Organic Synthesis at High Pressure, John Wiley, New York, 1991; (d) W. B. Holzapfel and N. S. Isaacs, (eds.) High-Pressure Techniques in Chemistry and Physics, a Practical Approach, Oxford University Press, Oxford, 1997; (e) R. van Eldik and C. D. Hubbard, (eds.) Chemistry under Extreme or Non-Classical Conditions, Wiley, New York, Spektrum, Heidelberg, 1997; (f) F-G. Klärner and M. K. Diedrich, The effect of pressure on reactions of dienes and polyenes, Chapter II in The chemistry of functional groups, the chemistry of dienes and polyenes, S. Patai and Z. Rappoport, (eds.), vol. 1, Wiley, New York, 1997.
24. Monographs: (a) N. S. Isaacs, Liquid Phase High Pressure Chemistry, John Wiley, Chichester, 1981; (b) W. J. le Noble, (ed.), Organic High Pressure Chemistry, Elsevier, Amsterdam, 1988; (c) K. Matsumoto and R. Morrin Acheson, (eds.) Organic Synthesis at High Pressure, John Wiley, New York, 1991; (d) W. B. Holzapfel and N. S. Isaacs, (eds.) High-Pressure Techniques in Chemistry and Physics, a Practical Approach, Oxford University Press, Oxford, 1997; (e) R. van Eldik and C. D. Hubbard, (eds.) Chemistry under Extreme or Non-Classical Conditions, Wiley, New York, Spektrum, Heidelberg, 1997; (f) F-G. Klärner and M. K. Diedrich, The effect of pressure on reactions of dienes and polyenes, Chapter II in The chemistry of functional groups, the chemistry of dienes and polyenes, S. Patai and Z. Rappoport, (eds.), vol. 1, Wiley, New York, 1997.
25. Monographs: (a) N. S. Isaacs, Liquid Phase High Pressure Chemistry, John Wiley, Chichester, 1981; (b) W. J. le Noble, (ed.), Organic High Pressure Chemistry, Elsevier, Amsterdam, 1988; (c) K. Matsumoto and R. Morrin Acheson, (eds.) Organic Synthesis at High Pressure, John Wiley, New York, 1991; (d) W. B. Holzapfel and N. S. Isaacs, (eds.) High-Pressure Techniques in Chemistry and Physics, a Practical Approach, Oxford University Press, Oxford, 1997; (e) R. van Eldik and C. D. Hubbard, (eds.) Chemistry under Extreme or Non-Classical Conditions, Wiley, New York, Spektrum, Heidelberg, 1997; (f) F-G. Klärner and M. K. Diedrich, The effect of pressure on reactions of dienes and polyenes, Chapter II in The chemistry of functional groups, the chemistry of dienes and polyenes, S. Patai and Z. Rappoport, (eds.), vol. 1, Wiley, New York, 1997.
26. Monographs: (a) N. S. Isaacs, Liquid Phase High Pressure Chemistry, John Wiley, Chichester, 1981; (b) W. J. le Noble, (ed.), Organic High Pressure Chemistry, Elsevier, Amsterdam, 1988; (c) K. Matsumoto and R. Morrin Acheson, (eds.) Organic Synthesis at High Pressure, John Wiley, New York, 1991; (d) W. B. Holzapfel and N. S. Isaacs, (eds.) High-Pressure Techniques in Chemistry and Physics, a Practical Approach, Oxford University Press, Oxford, 1997; (e) R. van Eldik and C. D. Hubbard, (eds.) Chemistry under Extreme or Non-Classical Conditions, Wiley, New York, Spektrum, Heidelberg, 1997; (f) F-G. Klärner and M. K. Diedrich, The effect of pressure on reactions of dienes and polyenes, Chapter II in The chemistry of functional groups, the chemistry of dienes and polyenes, S. Patai and Z. Rappoport, (eds.), vol. 1, Wiley, New York, 1997.
27. Reviews: (a) T. Asano and W. J. le Noble, Chem. Rev., 1978, 78, 407; (b) R. van Eldik, T. Asano and W. J. le Noble, Chem. Rev., 1989, 89, 549; (c) W. J. le Noble and H. Kelm, Angew. Chem., 1980, 92, 887; Angew. Chem., Int. Ed. Engl., 1980, 19, 841; (d) W. J. le Noble, Chem. Unserer Zeit, 1983, 17, 152; (e) G. Jenner, J Chem. Soc., Faraday Trans. 1, 1985, 81, 2437; (f) F.-G. Klärner, Chem. Unserer Zeit, 1989, 23, 53; (g) F-G. Klärner, V. Rüster, B. Zimny and D. Hochstrate, High Pressure Res., 1991, 7, 133; (h) N. S. Isaacs, Tetrahedron, 1991, 47, 8463.
28. Reviews: (a) T. Asano and W. J. le Noble, Chem. Rev., 1978, 78, 407; (b) R. van Eldik, T. Asano and W. J. le Noble, Chem. Rev., 1989, 89, 549; (c) W. J. le Noble and H. Kelm, Angew. Chem., 1980, 92, 887; Angew. Chem., Int. Ed. Engl., 1980, 19, 841; (d) W. J. le Noble, Chem. Unserer Zeit, 1983, 17, 152; (e) G. Jenner, J Chem. Soc., Faraday Trans. 1, 1985, 81, 2437; (f) F.-G. Klärner, Chem. Unserer Zeit, 1989, 23, 53; (g) F-G. Klärner, V. Rüster, B. Zimny and D. Hochstrate, High Pressure Res., 1991, 7, 133; (h) N. S. Isaacs, Tetrahedron, 1991, 47, 8463.
29. Reviews: (a) T. Asano and W. J. le Noble, Chem. Rev., 1978, 78, 407; (b) R. van Eldik, T. Asano and W. J. le Noble, Chem. Rev., 1989, 89, 549; (c) W. J. le Noble and H. Kelm, Angew. Chem., 1980, 92, 887; Angew. Chem., Int. Ed. Engl., 1980, 19, 841; (d) W. J. le Noble, Chem. Unserer Zeit, 1983, 17, 152; (e) G. Jenner, J Chem. Soc., Faraday Trans. 1, 1985, 81, 2437; (f) F.-G. Klärner, Chem. Unserer Zeit, 1989, 23, 53; (g) F-G. Klärner, V. Rüster, B. Zimny and D. Hochstrate, High Pressure Res., 1991, 7, 133; (h) N. S. Isaacs, Tetrahedron, 1991, 47, 8463.
30. Reviews: (a) T. Asano and W. J. le Noble, Chem. Rev., 1978, 78, 407; (b) R. van Eldik, T. Asano and W. J. le Noble, Chem. Rev., 1989, 89, 549; (c) W. J. le Noble and H. Kelm, Angew. Chem., 1980, 92, 887; Angew. Chem., Int. Ed. Engl., 1980, 19, 841; (d) W. J. le Noble, Chem. Unserer Zeit, 1983, 17, 152; (e) G. Jenner, J Chem. Soc., Faraday Trans. 1, 1985, 81, 2437; (f) F.-G. Klärner, Chem. Unserer Zeit, 1989, 23, 53; (g) F-G. Klärner, V. Rüster, B. Zimny and D. Hochstrate, High Pressure Res., 1991, 7, 133; (h) N. S. Isaacs, Tetrahedron, 1991, 47, 8463.
31. Reviews: (a) T. Asano and W. J. le Noble, Chem. Rev., 1978, 78, 407; (b) R. van Eldik, T. Asano and W. J. le Noble, Chem. Rev., 1989, 89, 549; (c) W. J. le Noble and H. Kelm, Angew. Chem., 1980, 92, 887; Angew. Chem., Int. Ed. Engl., 1980, 19, 841; (d) W. J. le Noble, Chem. Unserer Zeit, 1983, 17, 152; (e) G. Jenner, J Chem. Soc., Faraday Trans. 1, 1985, 81, 2437; (f) F.-G. Klärner, Chem. Unserer Zeit, 1989, 23, 53; (g) F-G. Klärner, V. Rüster, B. Zimny and D. Hochstrate, High Pressure Res., 1991, 7, 133; (h) N. S. Isaacs, Tetrahedron, 1991, 47, 8463.
32. Reviews: (a) T. Asano and W. J. le Noble, Chem. Rev., 1978, 78, 407; (b) R. van Eldik, T. Asano and W. J. le Noble, Chem. Rev., 1989, 89, 549; (c) W. J. le Noble and H. Kelm, Angew. Chem., 1980, 92, 887; Angew. Chem., Int. Ed. Engl., 1980, 19, 841; (d) W. J. le Noble, Chem. Unserer Zeit, 1983, 17, 152; (e) G. Jenner, J Chem. Soc., Faraday Trans. 1, 1985, 81, 2437; (f) F.-G. Klärner, Chem. Unserer Zeit, 1989, 23, 53; (g) F-G. Klärner, V. Rüster, B. Zimny and D. Hochstrate, High Pressure Res., 1991, 7, 133; (h) N. S. Isaacs, Tetrahedron, 1991, 47, 8463.
33. Reviews: (a) T. Asano and W. J. le Noble, Chem. Rev., 1978, 78, 407; (b) R. van Eldik, T. Asano and W. J. le Noble, Chem. Rev., 1989, 89, 549; (c) W. J. le Noble and H. Kelm, Angew. Chem., 1980, 92, 887; Angew. Chem., Int. Ed. Engl., 1980, 19, 841; (d) W. J. le Noble, Chem. Unserer Zeit, 1983, 17, 152; (e) G. Jenner, J Chem. Soc., Faraday Trans. 1, 1985, 81, 2437; (f) F.-G. Klärner, Chem. Unserer Zeit, 1989, 23, 53; (g) F-G. Klärner, V. Rüster, B. Zimny and D. Hochstrate, High Pressure Res., 1991, 7, 133; (h) N. S. Isaacs, Tetrahedron, 1991, 47, 8463.
34. Reviews: (a) T. Asano and W. J. le Noble, Chem. Rev., 1978, 78, 407; (b) R. van Eldik, T. Asano and W. J. le Noble, Chem. Rev., 1989, 89, 549; (c) W. J. le Noble and H. Kelm, Angew. Chem., 1980, 92, 887; Angew. Chem., Int. Ed. Engl., 1980, 19, 841; (d) W. J. le Noble, Chem. Unserer Zeit, 1983, 17, 152; (e) G. Jenner, J Chem. Soc., Faraday Trans. 1, 1985, 81, 2437; (f) F.-G. Klärner, Chem. Unserer Zeit, 1989, 23, 53; (g) F-G. Klärner, V. Rüster, B. Zimny and D. Hochstrate, High Pressure Res., 1991, 7, 133; (h) N. S. Isaacs, Tetrahedron, 1991, 47, 8463.
35. Reviews: (a) T. Asano and W. J. le Noble, Chem. Rev., 1978, 78, 407; (b) R. van Eldik, T. Asano and W. J. le Noble, Chem. Rev., 1989, 89, 549; (c) W. J. le Noble and H. Kelm, Angew. Chem., 1980, 92, 887; Angew. Chem., Int. Ed. Engl., 1980, 19, 841; (d) W. J. le Noble, Chem. Unserer Zeit, 1983, 17, 152; (e) G. Jenner, J Chem. Soc., Faraday Trans. 1, 1985, 81, 2437; (f) F.-G. Klärner, Chem. Unserer Zeit, 1989, 23, 53; (g) F-G. Klärner, V. Rüster, B. Zimny and D. Hochstrate, High Pressure Res., 1991, 7, 133; (h) N. S. Isaacs, Tetrahedron, 1991, 47, 8463.
36. Reviews: (a) K. Matsumoto, A. Sera and T. Uchida, Synthesis, 1985, 1; (b) K. Matsumoto and A. Sera, Synthesis, 1985, 999; (c) M. Ciobanu and K. Matsumoto, Liebigs Ann./Recl., 1997, 623.
37. Reviews: (a) K. Matsumoto, A. Sera and T. Uchida, Synthesis, 1985, 1; (b) K. Matsumoto and A. Sera, Synthesis, 1985, 999; (c) M. Ciobanu and K. Matsumoto, Liebigs Ann./Recl., 1997, 623.
38. Reviews: (a) K. Matsumoto, A. Sera and T. Uchida, Synthesis, 1985, 1; (b) K. Matsumoto and A. Sera, Synthesis, 1985, 999; (c) M. Ciobanu and K. Matsumoto, Liebigs Ann./Recl., 1997, 623.
39. 3SnH confirms this assumption.
40. The bromoalkene was prepared following a procedure in: K. Langer, Diploma Thesis, University of Münster, 1991.
41. M.-H. Lin, W. H. Watson, R. P. Kashyap and W. J. le Noble, J. Org. Chem., 1990, 55, 3597.
42. A. Rödig, Methoden Org. Chem. Houben-Weyl 4th Ed., 1952, 391.
43. The ketones were prepared following a procedure described in: P. Canone, G. B. Foscolos and G. Lemay, Tetrahedron Lett.. 1980, 21, 155.
44. F. D. Lewis, R. W. Johnson and D. E. Johnson, J. Am. Chem. Soc., 1974, 96, 6090.