Wet THF as a suitable solvent for a mild and convenient reduction of carbonyl compounds with NaBH4

Bulletin of the Chemical Society of Japan

Volumn 78, Issue 2, 2005, Pages 307-315

  Zeynizadeh, Behzad ^a   Behyar, Tarifeh ^a  

^a URMIA UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALDEHYDES; KETONES; REDUCTION; SODIUM COMPOUNDS; SOLVENTS;

ACYLOINS; CONJUGATED ENONES; REFLUX CONDITIONS; WET THF;

ORGANIC COMPOUNDS;

ALCOHOL; ALDEHYDE; CARBONYL DERIVATIVE; KETONE; SODIUM BOROHYDRIDE; SOLVENT; TOLUENE; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; TEMPERATURE;

EID: 14744282346     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.78.307     Document Type: Article

References (91)

1. a) M. Hudlicky, "Reductions in Organic Chemistry," Ellis Horwood Ltd., Chichester (1984).
2. b) J. Seyden-Penne, "Reductions by the Alumino and Borohydrides in Organic Synthesis," 2nd ed, Wiley-VCH, New York (1997).
3. c) R. C. Larock, "Comprehensive Organic Transformations: A Guide to Functional Group Preparations," 2nd ed, Wiley-VCH, New York (1999).
4. a) J. M. Lalancette, A. Freche, J. R. Bundle, and M. Laliberte, Synthesis, 1972, 526.
5. b) C. Narayana and M. Periasamy, Tetrahedron Lett., 26, 1757, 6361 (1985).
6. c) C. H. Rao, R. T. Chakrasali, H. Ila, and H. Junjappa, Tetrahedron, 46, 2195 (1990).
7. d) R. Koster, G. Seidel, R. Boses, and B. Wrackmeyer, Chem. Ber., 121, 1955 (1988).
8. e) C. F. Lane, Synthesis, 1975, 135.
9. a) B. C. Ranu, Synlett, 1993, 885.
10. b) S. Narasimhan and A. Balakumar, Aldrichimica Acta, 31, 19 (1998).
11. c) J. A. Cowan, Tetrahedron Lett., 27, 1205 (1986).
12. d) K. Soai and A. Ookawa, J. Org. Chem., 51, 4000 (1986).
13. e) M. E. Osborn, J. F. Pegues, and L. A. Paquette, J. Org. Chem., 45, 167 (1980).
14. a) G. Cainelli, D. Giacomini, and M. Panunzio, Tetrahedron, 41, 1385 (1985).
15. b) M. A. Makhlouf and B. Rickborn, J. Org. Chem., 46, 4810 (1981).
16. c) H. C. Brown, S. C. Kim, and S. Krishnamurthy, J. Org. Chem., 45, 1 (1980).
17. B. E. Blough and F. I. Carroll, Tetrahedron Lett., 34, 7239 (1993).
18. e) H. Firouzabadi, B. Tamami, and A. R. Kiasat, Phosphorus, Sulfur Silicon Relat. Elem., 159, 99 (2000).
19. f) H. Firouzabadi and M. Ghadami, Phosphorus, Sulfur Silicon Relat. Elem., 166, 83 (2000).
20. a) H. Firouzabadi, M. Adibi, and M. Ghadami, Phosphorus, Sulfur Silicon Relat. Elem., 142, 191 (1998).
21. b) H. Firouzabadi, M. Adibi, and B. Zeynizadeh, Synth. Commun., 28, 1257 (1998).
22. c) H. Firouzabadi and B. Zeynizadeh, Bull. Chem. Soc. Jpn., 70, 155 (1997).
23. d) B. Zeynizadeh, Bull. Chem. Soc. Jpn., 76, 317 (2003).
24. e) B. Zeynizadeh and F. Faraji, Bull. Korean Chem. Soc., 24, 453 (2003).
25. f) B. Zeynizadeh and K. Zahmatkesh, J. Chin. Chem. Soc., 50, 267 (2003).
26. g) B. Zeynizadeh and K. Zahmatkesh, J. Chin. Chem. Soc., 51, 801 (2004).
27. a) A. Giannis and K. Sandhoff, Angew. Chem., Int. Ed. Engl., 28, 218 (1989).
28. b) B. Ganem and J. O. Osby, Chem. Rev., 86, 763 (1986).
29. a) H. Firouzabadi and G. R. Afsharifar, Bull. Chem. Soc. Jpn., 68, 2595 (1995).
30. b) H. Firouzabadi and G. R. Afsharifar, Synth. Commun., 22, 497 (1992).
31. c) H. Firouzabadi and M. Adibi, Synth. Commun., 26, 2429 (1996).
32. d) H. Firouzabadi and M. Adibi, Phosphorus, Sulfur Silicon Relat. Elem., 142, 125 (1998).
33. a) H. Firouzabadi, B. Tamami, and N. Goudarzian, Synth. Commun., 21, 2275 (1991).
34. b) N. M. Yoon and J. Choi, Synlett, 1993, 135.
35. c) T. B. Sim, J. H. Ahn, and N. M. Yoon, Synthesis, 1996, 324.
36. d) J. W. Chen and C. Q. Qin, React. Polym., 16, 287 (1991).
37. H. Firouzabadi and B. Zeynizadeh, Iran. J. Sci. Technol. Trans. A, 19, 103 (1995).
38. a) Y. He, H. Zhao, X. Pan, and S. Wang, Synth. Commun., 19, 3047, 3051 (1989).
39. b) S. B. Mandel, B. Achari, and S. Chattopadhyay, Tetrahedron Lett., 33, 1647 (1992).
40. c) R. O. Hutchins, D. Kandasamy, F. Dux, III, C. A. Maraynoff, D. Rotstein, B. Goldsmith, W. Burgoyne, F. Cistone, J. Dalessandro, and J. Puglis, J. Org. Chem., 43, 2259 (1978).
41. d) K. Soai, H. Oyamada, M. Takase, and A. Ookawa, Bull. Chem. Soc. Jpn., 57, 1948 (1984).
42. e) A. Ookawa, H. Hiratsuka, and K. Soai, Bull. Chem. Soc. Jpn., 60, 1813 (1987).
43. f) D. E. Ward and C. K. Rhee, Can. J. Chem., 67, 1206 (1989).
44. g) D. E. Ward and C. K. Rhee, Synth. Commun., 18, 1927 (1988).
45. h) K. Soai, S. Yokoyama, and A. Ookawa, Synthesis, 1987, 48.
46. i) D. Dhawan and S. K. Grover, Synth. Commun., 22, 2405 (1992).
47. j) R. Lin and Y. Zhang, Synth. Commun., 17, 1403 (1987).
48. k) P.-D. Ren, S.-F. Pan, T.-W. Dong, and S.-H. Wu, Synth. Commun., 25, 3395 (1995).
49. l) M. R. Johnson and B. Rickborn, J. Org. Chem., 35, 1041 (1970).
50. m) C. Adams, V. Gold, and D. M. E. Reuben, J. Chem. Soc., Perkin Trans. 2, 1977, 1466.
51. n) A. Ookawa, S. Yokoyama, and K. Soai, Synth. Commun., 16, 819 (1986).
52. o) R. S. Varma and G. W. Kabalka, Synth. Commun., 15, 151 (1985).
53. p) A. Bianco, P. Passacantilli, and G. Righi, Synth. Commun., 18, 1765 (1998).
54. q) F. Rolla, J. Org. Chem., 47, 4327 (1982).
55. r) H. Seki, K. Koga, and S. Yamada, Chem. Pharm. Bull., 15, 1948 (1967).
56. B. Tamami and H. Mahdavi, Tetrahedron, 59, 821 (2003).
57. a) B. Zeynizadeh and S. Yahyaei, Z. Naturforsch., 59b, 699 (2004).
58. b) B. Zeynizadeh and S. Yahyaei, Bull. Korean Chem. Soc., 24, 1664 (2003).
59. c) B. Zeynizadeh and F. Shirini, Bull. Korean Chem. Soc., 24, 295 (2003).
60. d) B. Zeynizadeh and F. Shirini, J. Chem. Res., 2003, 335.
61. e) B. Zeynizadeh and S. Yahyaei, Z. Naturforsch., 59b, 704 (2004).
62. a) J. S. Cha, E. J. Kim, O. O. Kwon, and J. M. Kim, Bull. Korean Chem. Soc., 17, 50 (1996).
63. b) J. S. Cha, O. O. Kwon, S. Y. Kwon, J. M. Kim, W. W. Seo, and S. W. Chang, Bull. Korean Chem. Soc., 17, 221 (1996).
64. c) J. S. Cha, O. O. Kwon, and J. M. Kim, Bull. Korean Chem. Soc., 17, 725 (1996).
65. d) J. S. Cha, S. Y. Kwon, O. O. Kwon, J. M. Kim, and H. Song, Bull. Korean Chem. Soc., 17, 900 (1996).
66. a) C. F. Nutaitis and G. W. Gribble, Tetrahedron Lett., 24, 4287 (1983).
67. b) S. Kim, Y. J. Kim, C. H. Oh, and K. H. Ahn, Bull. Korean Chem. Soc., 5, 202 (1984).
68. B. C. Ranu and R. Chakraborty, Tetrahedron Lett., 31, 7663 (1990).
69. R. S. Varma and G. W. Kabalka, Synth. Commun., 15, 985 (1985).
70. C. F. Nutaitis and J. E. Bernardo, J. Org. Chem., 54, 5629 (1989).
71. a) S. Krishnamurthy and H. C. Brown, J. Org. Chem., 40, 1864 (1975).
72. b) S. Krishnamurthy and H. C. Brown, J. Org. Chem., 42, 1197 (1977).
73. S. Kim, Y. C. Moon, and K. H. Ahn, J. Org. Chem., 47, 3311 (1982).
74. a) E. J. Corey, K. B. Becker, and R. K. Varma, J. Am. Chem. Soc., 94, 8616 (1972).
75. b) J. C. Fuller, E. L. Stangeland, C. T. Goralski, and B. Singaram, Tetrahedron Lett., 34, 257 (1993).
76. c) B. Ganem, J. Org. Chem., 40, 146 (1975).
77. d) J. M. Fortunato and B. Ganem, J. Org. Chem., 41, 2194 (1976).
78. J. L. Luche, J. Am. Chem. Soc., 100, 2226 (1978).
79. A. L. Gemal and J. L. Luche, J. Am. Chem. Soc., 103, 5454 (1981).
80. H. Fujii, K. Oshima, and K. Utimoto, Chem. Lett., 1991, 1847.
81. K. S. Ravikumar, S. Baskaran, and S. Chandrasekaran, J. Org. Chem., 58, 5981 (1993).
82. A. R. Sande, M. H. Jagadale, R. B. Mane, and M. M. Salunkhe, Tetrahedron Lett., 25, 3501 (1984).
83. a) W. Kreiser, Ann. Chem., 745, 164 (1971).
84. b) V. H. Pechmann and F. Dahl, Chem. Ber., 23, 2421 (1890).
85. c) T.-L. Ho and G. A. Olah, Synthesis, 1976, 815.
86. d) T. Mori, T. Nakahara, and H. Nozaki, Can. J. Chem., 47, 3266 (1969).
87. e) R. Mayer, G. Hiller, M. Nitzschke, and J. Jentzsch, Angew. Chem., 75, 1011 (1963).
88. f) M. B. Rubin and J. M. Ben-Bassat, Tetrahedron Lett., 12, 3403 (1971).
89. M. Imuta and H. Ziffer, J. Org. Chem., 43, 3530 (1978).
90. a) A. T. Blomquist and A. Goldstein, Org. Synth., Coll. Vol., IV, 216 (1963).
91. b) J. P. Guette, N. Spassky, and D. Boucherot, Bull. Chem. Soc. Fr., 1972, 4217.