Selective conversion of aromatic nitriles to aldehydes by lithium N,N′-dimethylethylenediaminoaluminum hydride [3]

Bulletin of the Korean Chemical Society

Volumn 23, Issue 12, 2002, Pages 1697-1698

  Cha, Jin Soon ^a   Jang, Seung Ho ^a   Kwon, Sang Yong ^a  

^a Yeungnam University   (South Korea)

Author keywords

Aldehydes; Aromatic nitriles; Lithium dimethylethylenediaminoaluminum hydride; Selective reduction

Indexed keywords

ALDEHYDE; ALUMINUM HYDROXIDE; AROMATIC NITRO COMPOUND; BENZONITRILE; LITHIUM N,N' DIMETHYLETHYLENEDIAMINOALUMINUM HYDRIDE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; CHEMICAL REACTION; DERIVATIZATION; LETTER; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0037147601     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2002.23.12.1697     Document Type: Letter

References (38)

1. (a) Stannous chloride: Stephen, E. J. Chem. Soc. 1925, 127, 1874.
2. (b) Sodium triethoxyaluminohydride: Hesse, G.; Schrodel, R. Angew. Chem. 1956, 68, 438; Ann. 1957, 607, 24.
3. (b) Sodium triethoxyaluminohydride: Hesse, G.; Schrodel, R. Angew. Chem. 1956, 68, 438; Ann. 1957, 607, 24.
4. (c) Lithium triethoxyaluminohydride: Brown, H. C.; Schoaf, C. J.; Garg, C. P. Tetrahedron Lett. 1959, 9; Brown, H. C. J. Chem. Educ. 1961, 38, 173; Brown, H. C.; Garg, C. P. J. Am. Chem. Soc. 1964, 86, 1079, 1085; de Peretti, D.; Strzalko-Bottin, T.; Seydenpenne, J. Bull. Soc. Chim. Fr. 1974, 2925.
5. (c) Lithium triethoxyaluminohydride: Brown, H. C.; Schoaf, C. J.; Garg, C. P. Tetrahedron Lett. 1959, 9; Brown, H. C. J. Chem. Educ. 1961, 38, 173; Brown, H. C.; Garg, C. P. J. Am. Chem. Soc. 1964, 86, 1079, 1085; de Peretti, D.; Strzalko-Bottin, T.; Seydenpenne, J. Bull. Soc. Chim. Fr. 1974, 2925.
6. (c) Lithium triethoxyaluminohydride: Brown, H. C.; Schoaf, C. J.; Garg, C. P. Tetrahedron Lett. 1959, 9; Brown, H. C. J. Chem. Educ. 1961, 38, 173; Brown, H. C.; Garg, C. P. J. Am. Chem. Soc. 1964, 86, 1079, 1085; de Peretti, D.; Strzalko-Bottin, T.; Seydenpenne, J. Bull. Soc. Chim. Fr. 1974, 2925.
7. (c) Lithium triethoxyaluminohydride: Brown, H. C.; Schoaf, C. J.; Garg, C. P. Tetrahedron Lett. 1959, 9; Brown, H. C. J. Chem. Educ. 1961, 38, 173; Brown, H. C.; Garg, C. P. J. Am. Chem. Soc. 1964, 86, 1079, 1085; de Peretti, D.; Strzalko-Bottin, T.; Seydenpenne, J. Bull. Soc. Chim. Fr. 1974, 2925.
8. (d) Diisobutylaluminum hydride: Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR 1957, 116, 422; Minato, H.; Nagasaki, T. J. Chem. Soc. [c] 1966, 1866; Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pays-Bas 1966, 85, 343; Miller, A. E. G.; Bliss, J. W.; Schwartzman, L. H. J. Org. Chem. 1959, 24, 627; Teisseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44; Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org. Chem. 1970, 35, 186; Stevens, R. V.; Dupree, Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977; Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
9. (d) Diisobutylaluminum hydride: Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR 1957, 116, 422; Minato, H.; Nagasaki, T. J. Chem. Soc. [C] 1966, 1866; Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pays-Bas 1966, 85, 343; Miller, A. E. G.; Bliss, J. W.; Schwartzman, L. H. J. Org. Chem. 1959, 24, 627; Teisseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44; Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org. Chem. 1970, 35, 186; Stevens, R. V.; Dupree, Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977; Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
10. (d) Diisobutylaluminum hydride: Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR 1957, 116, 422; Minato, H.; Nagasaki, T. J. Chem. Soc. [C] 1966, 1866; Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pays-Bas 1966, 85, 343; Miller, A. E. G.; Bliss, J. W.; Schwartzman, L. H. J. Org. Chem. 1959, 24, 627; Teisseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44; Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org. Chem. 1970, 35, 186; Stevens, R. V.; Dupree, Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977; Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
11. (d) Diisobutylaluminum hydride: Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR 1957, 116, 422; Minato, H.; Nagasaki, T. J. Chem. Soc. [C] 1966, 1866; Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pays-Bas 1966, 85, 343; Miller, A. E. G.; Bliss, J. W.; Schwartzman, L. H. J. Org. Chem. 1959, 24, 627; Teisseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44; Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org. Chem. 1970, 35, 186; Stevens, R. V.; Dupree, Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977; Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
12. (d) Diisobutylaluminum hydride: Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR 1957, 116, 422; Minato, H.; Nagasaki, T. J. Chem. Soc. [C] 1966, 1866; Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pays-Bas 1966, 85, 343; Miller, A. E. G.; Bliss, J. W.; Schwartzman, L. H. J. Org. Chem. 1959, 24, 627; Teisseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44; Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org. Chem. 1970, 35, 186; Stevens, R. V.; Dupree, Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977; Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
13. (d) Diisobutylaluminum hydride: Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR 1957, 116, 422; Minato, H.; Nagasaki, T. J. Chem. Soc. [C] 1966, 1866; Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pays-Bas 1966, 85, 343; Miller, A. E. G.; Bliss, J. W.; Schwartzman, L. H. J. Org. Chem. 1959, 24, 627; Teisseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44; Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org. Chem. 1970, 35, 186; Stevens, R. V.; Dupree, Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977; Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
14. (d) Diisobutylaluminum hydride: Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR 1957, 116, 422; Minato, H.; Nagasaki, T. J. Chem. Soc. [C] 1966, 1866; Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pays-Bas 1966, 85, 343; Miller, A. E. G.; Bliss, J. W.; Schwartzman, L. H. J. Org. Chem. 1959, 24, 627; Teisseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44; Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org. Chem. 1970, 35, 186; Stevens, R. V.; Dupree, Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977; Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
15. (d) Diisobutylaluminum hydride: Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR 1957, 116, 422; Minato, H.; Nagasaki, T. J. Chem. Soc. [C] 1966, 1866; Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pays-Bas 1966, 85, 343; Miller, A. E. G.; Bliss, J. W.; Schwartzman, L. H. J. Org. Chem. 1959, 24, 627; Teisseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44; Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org. Chem. 1970, 35, 186; Stevens, R. V.; Dupree, Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977; Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
16. (e) Sodium diethylaluminohydride in the presence of 2,6-di-t-butylphenoxydiethylaluminum: Yoon, N. M.; Kim, S. K.; Gyong, Y. S. Bull. Korean Chem. Soc. 1986, 7, 323.
17. (f) Hydrogenation: Peitra, S.; Trinchera, C. Gazz. Chim. Ital. 1955, 85, 1705; Gaiffe, A.; Pallaud, R. Compt. Rend. 1961, 252, 1339, 1962, 254, 486.; Plieninger, H.; Werst, G. Angew Chem. 1955, 67, 156; Chem. Ber. 1955, 88, 1965.; Coker, J. N.; Kohlhase, W. L.; Fields, M.; Rogers, A. O.; Stevens, M. A. J. Org. Chem. 1962, 27, 850; Staskun, B.; Backeberg, O. G. J. Chem. Soc. 1964, 5880; van Es, T.; Staskun, B. J. Chem. Soc. 1965, 5775; Org. Syn. 1971, 51, 20.
18. (f) Hydrogenation: Peitra, S.; Trinchera, C. Gazz. Chim. Ital. 1955, 85, 1705; Gaiffe, A.; Pallaud, R. Compt. Rend. 1961, 252, 1339, 1962, 254, 486.; Plieninger, H.; Werst, G. Angew Chem. 1955, 67, 156; Chem. Ber. 1955, 88, 1965.; Coker, J. N.; Kohlhase, W. L.; Fields, M.; Rogers, A. O.; Stevens, M. A. J. Org. Chem. 1962, 27, 850; Staskun, B.; Backeberg, O. G. J. Chem. Soc. 1964, 5880; van Es, T.; Staskun, B. J. Chem. Soc. 1965, 5775; Org. Syn. 1971, 51, 20.
19. (f) Hydrogenation: Peitra, S.; Trinchera, C. Gazz. Chim. Ital. 1955, 85, 1705; Gaiffe, A.; Pallaud, R. Compt. Rend. 1961, 252, 1339, 1962, 254, 486.; Plieninger, H.; Werst, G. Angew Chem. 1955, 67, 156; Chem. Ber. 1955, 88, 1965.; Coker, J. N.; Kohlhase, W. L.; Fields, M.; Rogers, A. O.; Stevens, M. A. J. Org. Chem. 1962, 27, 850; Staskun, B.; Backeberg, O. G. J. Chem. Soc. 1964, 5880; van Es, T.; Staskun, B. J. Chem. Soc. 1965, 5775; Org. Syn. 1971, 51, 20.
20. (f) Hydrogenation: Peitra, S.; Trinchera, C. Gazz. Chim. Ital. 1955, 85, 1705; Gaiffe, A.; Pallaud, R. Compt. Rend. 1961, 252, 1339, 1962, 254, 486.; Plieninger, H.; Werst, G. Angew Chem. 1955, 67, 156; Chem. Ber. 1955, 88, 1965.; Coker, J. N.; Kohlhase, W. L.; Fields, M.; Rogers, A. O.; Stevens, M. A. J. Org. Chem. 1962, 27, 850; Staskun, B.; Backeberg, O. G. J. Chem. Soc. 1964, 5880; van Es, T.; Staskun, B. J. Chem. Soc. 1965, 5775; Org. Syn. 1971, 51, 20.
21. (f) Hydrogenation: Peitra, S.; Trinchera, C. Gazz. Chim. Ital. 1955, 85, 1705; Gaiffe, A.; Pallaud, R. Compt. Rend. 1961, 252, 1339, 1962, 254, 486.; Plieninger, H.; Werst, G. Angew Chem. 1955, 67, 156; Chem. Ber. 1955, 88, 1965.; Coker, J. N.; Kohlhase, W. L.; Fields, M.; Rogers, A. O.; Stevens, M. A. J. Org. Chem. 1962, 27, 850; Staskun, B.; Backeberg, O. G. J. Chem. Soc. 1964, 5880; van Es, T.; Staskun, B. J. Chem. Soc. 1965, 5775; Org. Syn. 1971, 51, 20.
22. (f) Hydrogenation: Peitra, S.; Trinchera, C. Gazz. Chim. Ital. 1955, 85, 1705; Gaiffe, A.; Pallaud, R. Compt. Rend. 1961, 252, 1339, 1962, 254, 486.; Plieninger, H.; Werst, G. Angew Chem. 1955, 67, 156; Chem. Ber. 1955, 88, 1965.; Coker, J. N.; Kohlhase, W. L.; Fields, M.; Rogers, A. O.; Stevens, M. A. J. Org. Chem. 1962, 27, 850; Staskun, B.; Backeberg, O. G. J. Chem. Soc. 1964, 5880; van Es, T.; Staskun, B. J. Chem. Soc. 1965, 5775; Org. Syn. 1971, 51, 20.
23. (f) Hydrogenation: Peitra, S.; Trinchera, C. Gazz. Chim. Ital. 1955, 85, 1705; Gaiffe, A.; Pallaud, R. Compt. Rend. 1961, 252, 1339, 1962, 254, 486.; Plieninger, H.; Werst, G. Angew Chem. 1955, 67, 156; Chem. Ber. 1955, 88, 1965.; Coker, J. N.; Kohlhase, W. L.; Fields, M.; Rogers, A. O.; Stevens, M. A. J. Org. Chem. 1962, 27, 850; Staskun, B.; Backeberg, O. G. J. Chem. Soc. 1964, 5880; van Es, T.; Staskun, B. J. Chem. Soc. 1965, 5775; Org. Syn. 1971, 51, 20.
24. (f) Hydrogenation: Peitra, S.; Trinchera, C. Gazz. Chim. Ital. 1955, 85, 1705; Gaiffe, A.; Pallaud, R. Compt. Rend. 1961, 252, 1339, 1962, 254, 486.; Plieninger, H.; Werst, G. Angew Chem. 1955, 67, 156; Chem. Ber. 1955, 88, 1965.; Coker, J. N.; Kohlhase, W. L.; Fields, M.; Rogers, A. O.; Stevens, M. A. J. Org. Chem. 1962, 27, 850; Staskun, B.; Backeberg, O. G. J. Chem. Soc. 1964, 5880; van Es, T.; Staskun, B. J. Chem. Soc. 1965, 5775; Org. Syn. 1971, 51, 20.
25. (f) Hydrogenation: Peitra, S.; Trinchera, C. Gazz. Chim. Ital. 1955, 85, 1705; Gaiffe, A.; Pallaud, R. Compt. Rend. 1961, 252, 1339, 1962, 254, 486.; Plieninger, H.; Werst, G. Angew Chem. 1955, 67, 156; Chem. Ber. 1955, 88, 1965.; Coker, J. N.; Kohlhase, W. L.; Fields, M.; Rogers, A. O.; Stevens, M. A. J. Org. Chem. 1962, 27, 850; Staskun, B.; Backeberg, O. G. J. Chem. Soc. 1964, 5880; van Es, T.; Staskun, B. J. Chem. Soc. 1965, 5775; Org. Syn. 1971, 51, 20.
26. (g) Organosilicon hydride: Fry, J. L. Chem. Comm. 1974, 45.; Fry, J. L.; Ott, R. A. J. Org. Chem. 1981, 46, 602.
27. (g) Organosilicon hydride: Fry, J. L. Chem. Comm. 1974, 45.; Fry, J. L.; Ott, R. A. J. Org. Chem. 1981, 46, 602.
28. (h) Thexylbromoborane-dimethyl sulfide: Cha, J, S.; Oh, S. Y.; Kim, J. E. Bull. Korean Chem. Soc. 1987, 8, 301.
29. (i) Potassium 9-sec-amyl-9-boratabicyclo[3.3.1]nonane: Cha, J. S.; Yoon, M. S. Tetrahedron Lett. 1989, 30, 3677.
30. (j) Lithium tris(dihexylamino)aluminum hydride: Cha, J. S.; Lee, S. E.; Lee, H. S. Org. Prep. Proced. Int. 1992, 24, 331;
31. Cha, J. S. Bull. Korean Chem. Soc. 1992, 13, 670.
32. (k) Sodium tris(dihexylamino)aluminum hydride: Cha, J. S.; Jeoung, M. K.; Kim, J. M.; Kwon, O. O.; Lee, J. C. Org. Prep. Proced. Int. 1994, 26, 552.
33. (l) Sodium diethylpiperidinohydroaluminate: Yoon, N. M.; An, D. K.; Jeong, K. H. Bull. Korean Chem. Soc. 1993, 14, 302.
34. (m) Diisobutylaluminum hydride-dimethyl sulfide complex: Cha, J. S.; Kwon, O. O.; Jeoung, M. K.; Kim, E. J. Bull. Korean Chem. Soc. 1994, 15, 1021.
35. (n) Catecholalane: Cha, J. S.; Chang, S. W.; Kwon, O. O.; Kim, J. M. Synlett 1996, 165.
36. 3+.
37. 4 and subjected to GC analysis to indicate the presence of benzaldehyde in yields of 98% and 99%, respectively (Table 1).
38. 4. The organic layer was then subjected to GC analysis for aldehydes. The combined GC analysis indicated a 98% yield of benzaldehyde and a 100% unreacted hexanenitrile.