Trimethylchlorosilane-modified Clemmensen reduction of metallocenyl ketones: Trapping and X-ray structures of aliphatic, olefinic, silylated pinacolic, and rearranged pinacolonic products

Journal of Organometallic Chemistry

Volumn 523, Issue 1, 1996, Pages 79-91

  Denifl, Peter ^a   Hradsky, Andreas ^a   Bildstein, Benno ^a   Wurst, Klaus ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

Clemmensen reduction; Ferrocene; Iron; Trimethylchlorosilane

Indexed keywords

EID: 0030568960     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(96)06344-9     Document Type: Article

References (54)

1. [1] (a) B.E. Maryanoff and A.B. Reitz, Chem. Rev., 89 (1989) 863.
2. (b) H.J. Bestmann and O. Vostrowsky, Top. Curr. Chem., 109 (1983) 85.
3. (c) H. Pommer and P.C. Thieme, Top. Curr. Chem., 109 (1983) 165.
4. (d) H. Pommer, Angew. Chem., 89 (1977) 437.
5. (e) A. Maercker, Org. React., 14 (1965) 270.
6. (f) J.I.G. Cadogan, Organophosphorus Reagents in Organic Synthesis, Academic Press, New York, 1979.
7. (g) A.W. Johnson, Ylid Chemistry, Academic Press, New York, 1979.
8. [2] (a) J.E. McMurry, Chem. Rev., 89 (1989) 1513.
9. (b) J.E. McMurry, Acc. Chem. Res., 16 (1983) 405.
10. (c) D. Lenoir, Synthesis, (1989) 883.
11. (d) D. Betschart and D. Seebach, Chimia, 43 (1989) 39.
12. [3] W.B. Motherwell and C.J. Nutley, Contemp. Org. Synth., 1 (1994) 219.
13. [4] B. Bildstein, P. Denifl, K. Wurst, M. André, M. Baumgarten, J. Friedrich and E. Ellmerer-Müller, Organometallics, 14 (1995) 4334.
14. [5] (a) C. Levanda, K. Beechgard and D.O. Cowan, J. Org. Chem., 16 (1976) 2700.
15. (b) M.D. Ward, Chem. Soc. Rev., (1995) 121.
16. [6] Part of this work has been presented as a poster at the 8th IUPAC Symp. Organometallic Chemistry Directed Towards Organic Synthesis, Santa Barbara, CA, USA, August 6-10, 1995.
17. [7] W.E. Watts, J Organomet. Chem. Libr., 7 (1979) 399.
18. [8] (a) C.L. Smith, J. Arnett and J. Ezike, J. Chem. Soc. Chem. Commun., (1980) 653.
19. (b) C.A.M. Alfonso, W.B. Motherwell and L.R. Roberts, Tetrahedron Lett., 33 (1992) 3367.
20. [9] W.B. Motherwell, Aldrichim. Acta, 25 (1992) 71.
21. [10] W. Ando and M. Ikeno, Chem. Lett., (1980) 1255.
22. [11] C.A.M. Alfonso, W.B. Motherwell, D.M. O'Shea and L.R. Roberts, Tetrahedron Lett., 33 (1992) 3899.
23. [12] A.K. Banerjee, M.C. Sulbaran de Carrasco, C.S.V. Frydrych-Houge and W.B. Motherwell, J. Chem. Soc. Chem. Commun., (1986) 1803.
24. [13] G.A. Risinger, E.W. Mach and K.W. Barnett, Chem. Ind., (1965) 679.
25. [14] A. Fürstner and A. Hupperts, J. Am. Chem. Soc., 117 (1995) 4468.
26. [15] J.-H. So, M.-K. Park and P. Boudjouk, J. Org. Chem., 53 (1988) 5871.
27. [16] (a) S.I. Goldberg, W.D. Bailey and M.L. McGregor, J. Org. Chem., 36 (1971) 761.
28. (b) S.I. Goldberg and W.D. Bailey J. Chem. Soc. Chem. Commun., (1969) 1059.
29. (c) S.I. Goldberg and M.L. McGregor, J. Org. Chem., 33 (1968) 2568.
30. [17] H. Paulus, K. Schlögl and W. Weissensteiner, Monatsh. Chem., 113 (1982) 767.
31. [18] D. Schütte, T. Oeser, H. Irgartinger and M. Wießler, Tetrahedron Lett., 36 (1995) 5163.
32. [19] W. Luef and R. Keese, Top Stereochem., 20 (1991) 231.
33. [20] J. Lukasser, H. Angleitner, H. Schottenberger, H. Kopacka, M. Schweiger, B. Bildstein, K.-H. Ongania and K. Wurst, Organometallics, 14 (1995) 5566.
34. [21] R.E. Hester and M. Cais, J. Organomet. Chem., 16 (1969) 283.
35. [22] D.E. Bublitz and K.L. Rinehart, Jr., in G. Dauben, R. Adams, A.H. Blatt, V. Boekelheide, T.L. Cains, D.J. Cram and H.O. House (eds.), Organic Reactions, Vol. 17, Wiley, New York, 1969, pp. 1-154.
36. [23] M.D. Rausch and M. Vogel, J. Org. Chem., 22 (1957) 903.
37. [24] (a) I. Goldberg, J. Org. Chem., 25 (1960) 482.
38. (b) M.D. Rausch, E.O. Fischer and H. Grubert, J. Am. Chem. Soc., 82 (1960) 76.
39. [25] E.W. Neuse and R.M. Trahe, J. Macromol. Chem., 1 (3) (1966) 611.
40. [26] (a) M. Rosenblum, J. Am. Chem. Soc., 81 (1959) 4530.
41. (b) M. Cais, A. Modiano and A. Raveh, J. Am. Chem. Soc., 87 (1965) 5607.
42. (c) M. Cais and A. Eisenstadt, J. Org. Chem., 30 (1965) 1148.
43. [27] International Tables for X-ray Crystallography, Vol. IV, Kynoch, Birmingham, 1974, pp. 72-98.
44. [28] (a) A.C.T. North, D. Phillips and F.S. Mathews, Acta Crystallogr. Sect. A:, 24 (1968) 351.
45. (b) N. Walker and D. Stuart, Acta Crystallogr. Sect. A:, 39 (1983) 158.
46. [29] G.M. Sheldrick, SHELXS-86 Program for Crystal Structure Solutions, Göttingen, 1986.
47. [30] G.M. Sheldrick, SHELXL-93 Program for the Refinement of Crystal Structures, Göttingen, 1993.
48. [31] (a) P.L. Pauson and W.E. Watts, J. Chem. Soc., (1963) 2990.
49. (b) R. Eberhardt, H. Lehner and K. Schlögl, Monatsh. Chem., 104 (1973) 1409.
50. (c) K. Schlögl and H. Egger, Ann. Chem., 676 (1964) 76.
51. (d) V.I. Boev, Zh. Oshch. Khim., 46 (1976) 1838.
52. [32] M. Rosenblum and R.B. Woodward, J. Am. Chem. Soc., 80 (1958) 5443.
53. [33] (a) M. Vogel, M. Rausch and H. Rosenberg, J. Org. Chem., 22 (1957) 1016.
54. (b) K. Schlögl, A. Mohar and M. Peterlik, Monatsh. Chem., 92 (1961) 921.