Facile synthesis of nitriles from primary nitro compounds via nitrolic acids and their esters

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7791-7794

  Chang, Rae Kyu ^a   Kim, Kyongtae ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

NITRILE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030597103     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01779-0     Document Type: Article

References (18)

1. 1. Mukaiyama, T; Nambu, H. J. Org. Chem, 1962, 27, 2201-2204.
2. 2. Skaramstad, J. Acta Chem. Scand. 1970, 24, 3424-3426.
3. 3. Denis, J. N.; Krief, A. Tetrahedron Lett. 1979, 41, 3995-3996.
4. 4. Denis, J. N.; Krief, A. J. Chem. Soc., Chem. Commun. 1980, 544-545.
5. 5. Olah, G. A.; Vankar, Y. D.; Gupta, B. G. B. Synthesis, 1979, 36-37.
6. 6. Olah, G. A.; Narang, S.C.; Field, L. D.:Fung, A. P. J. Org. Chem. 1983, 48, 2766-2767.
7. 7. Albanese, D.; Landini, D.; Penso, M.; Pozzi, G. Synth. Commun. 1990, 20, 965-971.
8. 8. Tsay, S.-C.; Gani, P.; Hwu, J. R. J. Chem. Soc., Perkin Trans. 1 1991, 1493-1495.
9. 9. Chang, R.; Kim, K. Bull. Korean Chem. Soc. 1995, 16, 475-476.
10. 10. Ono, N.; Miyake, H.; Kamimura, A.; Hamamoto, I; Tamura, R.; Kaji, A. Tetrahedron 1985, 41, 4013-4023.
11. 11. Boivin, J.; Schiano, A.-M.; Zard, S. Z. Tetrahedron Lett. 1994, 35, 249-252.
12. 3: C, 69.97; H, 3.82; N, 12.24; Found: C, 70.09; H, 4.16; N, 12.36.
13. -1. Elution next with the same solvent mixture (2:1, 100 mL) gave 5 (52 mg, 100%).
14. 3: C, 55.66; H, 5.19; N, 14.43; Found: C, 55.52; H, 5.11; N, 14.17.
15. 4: C, 70.58; H, 4.85; N, 7.48 ; Found: C, 70.54; H, 4.87; N, 7.45.
16. 4Si: C, 55.53; H, 7.46; N, 8.63 ; Found: C, 55.70; H, 7.55; N, 8.47.
17. 17. (a) Nelsen, S. F. in Free Radicals, Kochi, J. K. Ed.; John Wiley and Sons Inc.: New York, 1973, Vol II, Chap. 21, pp 527-593.
18. (b) Forrester, A. R. in International Review of Science, Organic Chemistry Series Two: Free Radical Reactions, Butterworths Co.: London, 1975, Vol. 10, Chap. 5, pp 87-131.