Nitrolic acids: Efficient precursors of nitrile oxides under neutral conditions

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1191-1194

  Matt, Christophe ^a   Gissot, Arnaud ^a   Wagner, Alain ^a   Mioskowski, Charles ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Alkyl halides; Cycloadditions; Nitrile oxides; Nitro compounds; Nitrolic acids

Indexed keywords

HALIDE; NITRILE; NITRO DERIVATIVE; OXIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034685216     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02278-9     Document Type: Article

References (23)

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3. Godt, H. C.; Quinn, J. F. J. Am. Chem. Soc. 1956, 78, 1461-1464. Khmel'nitskii, L. I.; Novikov, S. S.; Lebedev, O. V. Izvest. Akad. Nauk. SSSR. 1961, 477-482 (Chem. Abstr. 1961, 55, 2389). Egan, C.; Clery, M.; Hegarty, A. F.; Welch, A. J. J. Chem. Soc., Perkin Trans. 1 1991, 249-256. Makhova, N. N.; Ovchinikov, I. V.; Dubonos, V. G.; Strelenko, Y. A.; Khmel'nitsii, L. I. J. Chem. Soc. Mendeleev Commun. 1992, 91-92. Chang, K. R.; Kim, K. Tetrahedron Lett. 1996, 37, 7791-7794.
4. Godt, H. C.; Quinn, J. F. J. Am. Chem. Soc. 1956, 78, 1461-1464. Khmel'nitskii, L. I.; Novikov, S. S.; Lebedev, O. V. Izvest. Akad. Nauk. SSSR. 1961, 477-482 (Chem. Abstr. 1961, 55, 2389). Egan, C.; Clery, M.; Hegarty, A. F.; Welch, A. J. J. Chem. Soc., Perkin Trans. 1 1991, 249-256. Makhova, N. N.; Ovchinikov, I. V.; Dubonos, V. G.; Strelenko, Y. A.; Khmel'nitsii, L. I. J. Chem. Soc. Mendeleev Commun. 1992, 91-92. Chang, K. R.; Kim, K. Tetrahedron Lett. 1996, 37, 7791-7794.
5. Godt, H. C.; Quinn, J. F. J. Am. Chem. Soc. 1956, 78, 1461-1464. Khmel'nitskii, L. I.; Novikov, S. S.; Lebedev, O. V. Izvest. Akad. Nauk. SSSR. 1961, 477-482 (Chem. Abstr. 1961, 55, 2389). Egan, C.; Clery, M.; Hegarty, A. F.; Welch, A. J. J. Chem. Soc., Perkin Trans. 1 1991, 249-256. Makhova, N. N.; Ovchinikov, I. V.; Dubonos, V. G.; Strelenko, Y. A.; Khmel'nitsii, L. I. J. Chem. Soc. Mendeleev Commun. 1992, 91-92. Chang, K. R.; Kim, K. Tetrahedron Lett. 1996, 37, 7791-7794.
6. Godt, H. C.; Quinn, J. F. J. Am. Chem. Soc. 1956, 78, 1461-1464. Khmel'nitskii, L. I.; Novikov, S. S.; Lebedev, O. V. Izvest. Akad. Nauk. SSSR. 1961, 477-482 (Chem. Abstr. 1961, 55, 2389). Egan, C.; Clery, M.; Hegarty, A. F.; Welch, A. J. J. Chem. Soc., Perkin Trans. 1 1991, 249-256. Makhova, N. N.; Ovchinikov, I. V.; Dubonos, V. G.; Strelenko, Y. A.; Khmel'nitsii, L. I. J. Chem. Soc. Mendeleev Commun. 1992, 91-92. Chang, K. R.; Kim, K. Tetrahedron Lett. 1996, 37, 7791-7794.
7. Godt, H. C.; Quinn, J. F. J. Am. Chem. Soc. 1956, 78, 1461-1464. Khmel'nitskii, L. I.; Novikov, S. S.; Lebedev, O. V. Izvest. Akad. Nauk. SSSR. 1961, 477-482 (Chem. Abstr. 1961, 55, 2389). Egan, C.; Clery, M.; Hegarty, A. F.; Welch, A. J. J. Chem. Soc., Perkin Trans. 1 1991, 249-256. Makhova, N. N.; Ovchinikov, I. V.; Dubonos, V. G.; Strelenko, Y. A.; Khmel'nitsii, L. I. J. Chem. Soc. Mendeleev Commun. 1992, 91-92. Chang, K. R.; Kim, K. Tetrahedron Lett. 1996, 37, 7791-7794.
8. Matt, C.; Wagner, A.; Mioskowski, C. J. Org. Chem. 1997, 62, 234-235.
9. Wieland, H.; Semper, L. Ber. 1906, 39, 2522-2526. Grundmann, C.; Grünanger, P. The Nitrile Oxides; Springer: New York, 1971; pp. 51-52.
10. Wieland, H.; Semper, L. Ber. 1906, 39, 2522-2526. Grundmann, C.; Grünanger, P. The Nitrile Oxides; Springer: New York, 1971; pp. 51-52.
11. Preparation of nitrolic acids: Primary nitroalkanes or primary alkyl bromides (1 mmol) were reacted in DMSO (2 mL) in the presence of acetic acid (10 mmol) and sodium nitrite (3 mmol) at room temperature. After about one hour, ether (25 mL) was added to the reaction mixture and the organic layer washed successively with a 10% hydrochloric acid aqueous solution and a sodium bicarbonate saturated solution. The organic layer was then dried over magnesium sulfate and concentrated under vacuum. The crude mixture that usually displayed over 80% purity in nitrolic acid could be purified by silica gel chromatography or directly involved in the cycloaddition step.
12. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 53, 476-478. Moriya, O.; Takenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans. 1 1994, 413-416. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342. Bachman, G. B.; Strom, L. E. J. Org. Chem. 1963, 28, 1150-1152. McKillop, A.; Kobylecki, R. J. Tetrahedron 1974, 30, 1365-1371. Harada, K.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Shimizu, T.; Hayashi, Y.; Shibafushi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831. Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547-1550.
13. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 53, 476-478. Moriya, O.; Takenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans. 1 1994, 413-416. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342. Bachman, G. B.; Strom, L. E. J. Org. Chem. 1963, 28, 1150-1152. McKillop, A.; Kobylecki, R. J. Tetrahedron 1974, 30, 1365-1371. Harada, K.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Shimizu, T.; Hayashi, Y.; Shibafushi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831. Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547-1550.
14. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 53, 476-478. Moriya, O.; Takenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans. 1 1994, 413-416. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342. Bachman, G. B.; Strom, L. E. J. Org. Chem. 1963, 28, 1150-1152. McKillop, A.; Kobylecki, R. J. Tetrahedron 1974, 30, 1365-1371. Harada, K.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Shimizu, T.; Hayashi, Y.; Shibafushi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831. Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547-1550.
15. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 53, 476-478. Moriya, O.; Takenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans. 1 1994, 413-416. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342. Bachman, G. B.; Strom, L. E. J. Org. Chem. 1963, 28, 1150-1152. McKillop, A.; Kobylecki, R. J. Tetrahedron 1974, 30, 1365-1371. Harada, K.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Shimizu, T.; Hayashi, Y.; Shibafushi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831. Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547-1550.
16. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 53, 476-478. Moriya, O.; Takenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans. 1 1994, 413-416. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342. Bachman, G. B.; Strom, L. E. J. Org. Chem. 1963, 28, 1150-1152. McKillop, A.; Kobylecki, R. J. Tetrahedron 1974, 30, 1365-1371. Harada, K.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Shimizu, T.; Hayashi, Y.; Shibafushi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831. Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547-1550.
17. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 53, 476-478. Moriya, O.; Takenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans. 1 1994, 413-416. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342. Bachman, G. B.; Strom, L. E. J. Org. Chem. 1963, 28, 1150-1152. McKillop, A.; Kobylecki, R. J. Tetrahedron 1974, 30, 1365-1371. Harada, K.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Shimizu, T.; Hayashi, Y.; Shibafushi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831. Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547-1550.
18. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 53, 476-478. Moriya, O.; Takenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans. 1 1994, 413-416. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342. Bachman, G. B.; Strom, L. E. J. Org. Chem. 1963, 28, 1150-1152. McKillop, A.; Kobylecki, R. J. Tetrahedron 1974, 30, 1365-1371. Harada, K.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Shimizu, T.; Hayashi, Y.; Shibafushi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831. Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547-1550.
19. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 53, 476-478. Moriya, O.; Takenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans. 1 1994, 413-416. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342. Bachman, G. B.; Strom, L. E. J. Org. Chem. 1963, 28, 1150-1152. McKillop, A.; Kobylecki, R. J. Tetrahedron 1974, 30, 1365-1371. Harada, K.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Shimizu, T.; Hayashi, Y.; Shibafushi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831. Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547-1550.
20. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 53, 476-478. Moriya, O.; Takenaka, H.; Iyoda, M.; Urata, Y.; Endo, T. J. Chem. Soc., Perkin Trans. 1 1994, 413-416. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342. Bachman, G. B.; Strom, L. E. J. Org. Chem. 1963, 28, 1150-1152. McKillop, A.; Kobylecki, R. J. Tetrahedron 1974, 30, 1365-1371. Harada, K.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Shimizu, T.; Hayashi, Y.; Shibafushi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831. Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547-1550.
21. Leslie-Smith, M. G.; Paton, R. M.; Webb, N. Tetrahedron Lett. 1994, 35, 9251-9254. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Harada, H.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303.
22. Leslie-Smith, M. G.; Paton, R. M.; Webb, N. Tetrahedron Lett. 1994, 35, 9251-9254. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Harada, H.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303.
23. Leslie-Smith, M. G.; Paton, R. M.; Webb, N. Tetrahedron Lett. 1994, 35, 9251-9254. Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534. Harada, H.; Kaji, E.; Zen, S. Chem. Pharm. Bull. 1980, 28, 3296-3303.