Simple reduction of ferrocenyl aldehydes and ketones by sodium boranuide in trifluoroacetic acid: New, efficient, general preparation of alkylferrocenes

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 12, 1996, Pages 1381-1383

  Bhattacharyya, Sukanta ^a,b  

^a Vijoygarh College   (India)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748906263     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001381     Document Type: Article

References (58)

1. See, for example: A. M. Giroud-Godquin and P. M. Maitlis, Angew. Chem., Int. Ed. Engl., 1991, 30, 375;
2. A. Ulman, An Introduction to Ultrathin Organic Films from Langmuir-Blodgett to Self-Assembly, Academic Press, Boston, MA, 1991;
3. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science, ed. A. Togni and T. Hayashi, VCH Verlagsgesellschaft, Weinheim, 1995.
4. For some of the leading references, see: Y. Degani and A. Heller, J. Phys. Chem., 1987, 91, 1285;
5. H. A. U. Hill, D. J. Page and N. J. Walton, J. Electroanal. Chem. Interfacial Electrochem., 1987, 217, 141;
6. K. Uosaki, Y. Sato and H. Kita, Langmuir, 1991, 7, 1510;
7. P. D. Beer, Z. Chen, M. G. B. Drew, J. Kingston, M. Ogden and P. Spencer, J. Chem. Soc., Chem. Commun., 1993, 1046;
8. C. D. Hall, J. H. R. Tucker, S. Y. F. Chu, A. W. Parkins and S. C. Nyburg, J. Chem. Soc., Chem. Commun., 1993, 1505;
9. J. L. Fillaut, J. Linares and D. Astruc, Angew. Chem., Int. Ed. Engl., 1994, 33, 2460;
10. G. K. Rowe and S. E. Creager, Langmuir, 1994, 10, 1186;
11. R. Deschenaux and J. Santiago, Tetrahedron Lett., 1994, 35, 2169;
12. J. T. Yli-Kauhaluoma, J. A. Ashley, C. H. Lo, L. Tucker, M. M. Wolfe and K. D. Janda, J. Am. Chem. Soc., 1995, 117, 7041;
13. T. J. Gardner, C. D. Frisbie and M. S. Wrighton, J. Am. Chem. Soc., 1995, 117, 6927 and references therein;
14. A. Riklin, E. Katz, I. Willner, A. Stocker and A. F. Bueckmann, Nature, 1995, 376, 672.
15. M. Vogel, M. D. Rausch and H. Rosenberg, J. Org. Chem., 1957, 22, 1016;
16. A. N. Nesmeyanov and N. S. Kochetkova, Dokl. Akad. Nauk SSSR, 1956, 109, 543
17. (Chem. Abstr., 1957, 51, 5057);
18. Chem. Abstr., 1957, 114, 800
19. (Chem. Abstr., 1958, 52, 3794);
20. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1958, 242
21. (Chem. Abstr., 1958, 52, 12 852);
22. E. W. Neuse and D. S. Trifan, J. Am. Chem. Soc., 1962, 84, 1850;
23. D. E. Bublitz, Can. J. Chem., 1964, 42, 2381.
24. M. Rosenblum, Chemistry of the Iron Group Metallocenes: ferrocene, ruthenocene, osmocene, Wiley, New York, 1965, Pt. 1, pp. 62-119 and references therein;
25. D. E. Bublitz and K. L. Rinehart, Jr., Org. React., 1969, 17, 24.
26. M. Rosenblum, Chemistry of the Iron Group Metallocenes: ferrocene, ruthenocene, osmocene, Wiley, New York, 1965, Pt. 1, p. 146;
27. D. E. Bublitz and K. L. Rinehart, Jr., Org. React., 1969, 17, 28.
28. (a) M. D. Rausch, M. Vogel and H. Rosenberg, J. Org. Chem., 1957, 22, 903;
29. (b) K. L. Rinehart, R. J. Curby and P. E. Sokol, J. Am. Chem. Soc., 1957, 79, 3420;
30. (c) M. Rosenblum and R. B. Woodward, J. Am. Chem. Soc., 1958, 80, 5443;
31. (d) K. Schloegl and A. Mohar, Monatsh. Chem., 1961, 92, 219.
32. (a) N. Weliky and E. S. Gould, J. Am. Chem. Soc., 1957, 79, 2742;
33. (b) E. L. DeYoung, J. Org. Chem., 1961, 26, 1312;
34. (c) J. M. Osgerby and P. L. Pauson, J. Chem. Soc., 1961, 4604;
35. (d) M. Rosenblum, A. K. Banerjee, N. Danieli, R. W. Fish and V. Schlatter, J. Am. Chem. Soc., 1963, 85, 316;
36. (e) P. L. Pauson and W. E. Watts, J. Chem. Soc., 1962, 3880.
37. (a) K. L. Rinehart, A. F. Ellis, C. J. Michejda and P. A. Kittle, J. Am. Chem. Soc., 1960, 82, 4112;
38. (b) K. Schloegl, A. Mohar and M. Peterlik, Monatsh. Chem., 1961, 92, 921;
39. (c) K. Schloegl and A. Mohar, Monatsh. Chem., 1962, 93, 861.
40. S. Bhattacharyya, A. Chatterjee and S. K. Duttachowdhury, J. Chem. Soc., Perkin Trans. 1, 1994, 1;
41. S. Bhattacharyya, Tetrahedron Lett., 1994, 35, 2401;
42. Synlett, 1994, 1029;
43. J. Org. Chem., 1995, 60, 4928;
44. J. Chem. Soc., Perkin Trans. 1, 1995, 1845;
45. Synlett, 1995, 971.
46. For a review, see: G. W. Gribble and C. F. Nutaitis, Org. Prep. Proced. Int., 1985, 17, 317.
47. M. Cais, Organomet. Chem. Rev., 1966, 1, 435;
48. J. Feinberg and M. Rosenblum, J. Am. Chem. Soc., 1969, 91, 4324;
49. T. D. Turbitt and W. E. Watts, J. Chem. Soc., Chem. Commun., 1973, 182.
50. Y. Ito, T. Konoike, T. Harada and T. Saegusa, J. Am. Chem. Soc., 1977, 99, 1487.
51. P. J. Graham, R. V. Lindsey, G. W. Parshall, M. L. Peterson and G. M. Whitman, J. Am. Chem. Soc., 1957, 79, 3416.
52. L. A. Day, Br. Pat. 864 198, 1961 (Chem. Abstr., 1961, 55, 17 647).
53. (a) A. L. J. Beckwith and R. J. Leydon, Tetrahedron Lett., 1963, 385;
54. (b) B. F. Hallam and P. L. Pauson, J. Chem. Soc., 1956, 3030.
55. J. B. Thompson, Chem. Ind. (London), 1959, 1122.
56. E. A. Hill and J. H. Richards, J. Am. Chem. Soc., 1961, 83, 4216.
57. K. Schoegl and H. Seiler, Monatsh. Chem., 1960, 91, 79;
58. Angew. Chem., 1960, 72, 38.