Novel Transformation of Primary Nitroalkanes and Primary Alkyl Bromides to the Corresponding Carboxylic Acids

Journal of Organic Chemistry

Volumn 62, Issue 2, 1997, Pages 234-235

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

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000083032     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962110n     Document Type: Article

References (31)

1. Larson, J. H. The Chemistry of Nitro and Nitroso Groups, Methods of Formation of Nitro Group in Aliphatic and Alicyclic Systems; Pataï, S., Ed.; Interscience Publishers: New York, 1969; Part 1, pp 301-348. Seebach, D.; Colwin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1-17. Rosini, G.; Ballini R. Synthesis 1988, 833-847.
2. Larson, J. H. The Chemistry of Nitro and Nitroso Groups, Methods of Formation of Nitro Group in Aliphatic and Alicyclic Systems; Pataï, S., Ed.; Interscience Publishers: New York, 1969; Part 1, pp 301-348. Seebach, D.; Colwin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1-17. Rosini, G.; Ballini R. Synthesis 1988, 833-847.
3. Larson, J. H. The Chemistry of Nitro and Nitroso Groups, Methods of Formation of Nitro Group in Aliphatic and Alicyclic Systems; Pataï, S., Ed.; Interscience Publishers: New York, 1969; Part 1, pp 301-348. Seebach, D.; Colwin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1-17. Rosini, G.; Ballini R. Synthesis 1988, 833-847.
4. Nef, J. V. Ann. Chem. 1899, 308, 264-333. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367-4373. Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1965, 87, 1742-1747. Kornblum, N.; Wade, P. A. J. Org. Chem. 1973, 38, 1418-1420. Olah, G. A.; Gupta, B. Synthesis 1980, 44-45. McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259-260. For a review of the Nef reaction, see: Pinnick, H. W. Org. React. 1990, 38, 655-792.
5. Nef, J. V. Ann. Chem. 1899, 308, 264-333. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367-4373. Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1965, 87, 1742-1747. Kornblum, N.; Wade, P. A. J. Org. Chem. 1973, 38, 1418-1420. Olah, G. A.; Gupta, B. Synthesis 1980, 44-45. McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259-260. For a review of the Nef reaction, see: Pinnick, H. W. Org. React. 1990, 38, 655-792.
6. Nef, J. V. Ann. Chem. 1899, 308, 264-333. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367-4373. Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1965, 87, 1742-1747. Kornblum, N.; Wade, P. A. J. Org. Chem. 1973, 38, 1418-1420. Olah, G. A.; Gupta, B. Synthesis 1980, 44-45. McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259-260. For a review of the Nef reaction, see: Pinnick, H. W. Org. React. 1990, 38, 655-792.
7. Nef, J. V. Ann. Chem. 1899, 308, 264-333. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367-4373. Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1965, 87, 1742-1747. Kornblum, N.; Wade, P. A. J. Org. Chem. 1973, 38, 1418-1420. Olah, G. A.; Gupta, B. Synthesis 1980, 44-45. McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259-260. For a review of the Nef reaction, see: Pinnick, H. W. Org. React. 1990, 38, 655-792.
8. Nef, J. V. Ann. Chem. 1899, 308, 264-333. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367-4373. Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1965, 87, 1742-1747. Kornblum, N.; Wade, P. A. J. Org. Chem. 1973, 38, 1418-1420. Olah, G. A.; Gupta, B. Synthesis 1980, 44-45. McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259-260. For a review of the Nef reaction, see: Pinnick, H. W. Org. React. 1990, 38, 655-792.
9. Nef, J. V. Ann. Chem. 1899, 308, 264-333. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367-4373. Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1965, 87, 1742-1747. Kornblum, N.; Wade, P. A. J. Org. Chem. 1973, 38, 1418-1420. Olah, G. A.; Gupta, B. Synthesis 1980, 44-45. McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259-260. For a review of the Nef reaction, see: Pinnick, H. W. Org. React. 1990, 38, 655-792.
10. Nef, J. V. Ann. Chem. 1899, 308, 264-333. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367-4373. Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1965, 87, 1742-1747. Kornblum, N.; Wade, P. A. J. Org. Chem. 1973, 38, 1418-1420. Olah, G. A.; Gupta, B. Synthesis 1980, 44-45. McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259-260. For a review of the Nef reaction, see: Pinnick, H. W. Org. React. 1990, 38, 655-792.
11. Grundmann, C.; Ruske, W. Chem. Ber. 1953, 86, 939-943. Parham, W. E.; Ramp, F. L. J. Am. Chem. Soc. 1951, 73, 1293-1295. Noyce, W. K.; Coleman, C. H.; Barr, J. T. J. Am. Chem. Soc. 1951, 73, 1295-1296. Stilles, M.; Finkbeiner H. L. J. Am. Chem. Soc. 1959, 81, 505-506. Corey E. J.; Andersen N. H.; Carlson, R. M.; Paust, J.; Vedejs, E.; Vlattas I.; Winter, R. E. K. J. Am. Chem. Soc. 1968, 90, 3245-3247.
12. Grundmann, C.; Ruske, W. Chem. Ber. 1953, 86, 939-943. Parham, W. E.; Ramp, F. L. J. Am. Chem. Soc. 1951, 73, 1293-1295. Noyce, W. K.; Coleman, C. H.; Barr, J. T. J. Am. Chem. Soc. 1951, 73, 1295-1296. Stilles, M.; Finkbeiner H. L. J. Am. Chem. Soc. 1959, 81, 505-506. Corey E. J.; Andersen N. H.; Carlson, R. M.; Paust, J.; Vedejs, E.; Vlattas I.; Winter, R. E. K. J. Am. Chem. Soc. 1968, 90, 3245-3247.
13. Grundmann, C.; Ruske, W. Chem. Ber. 1953, 86, 939-943. Parham, W. E.; Ramp, F. L. J. Am. Chem. Soc. 1951, 73, 1293-1295. Noyce, W. K.; Coleman, C. H.; Barr, J. T. J. Am. Chem. Soc. 1951, 73, 1295-1296. Stilles, M.; Finkbeiner H. L. J. Am. Chem. Soc. 1959, 81, 505-506. Corey E. J.; Andersen N. H.; Carlson, R. M.; Paust, J.; Vedejs, E.; Vlattas I.; Winter, R. E. K. J. Am. Chem. Soc. 1968, 90, 3245-3247.
14. Grundmann, C.; Ruske, W. Chem. Ber. 1953, 86, 939-943. Parham, W. E.; Ramp, F. L. J. Am. Chem. Soc. 1951, 73, 1293-1295. Noyce, W. K.; Coleman, C. H.; Barr, J. T. J. Am. Chem. Soc. 1951, 73, 1295-1296. Stilles, M.; Finkbeiner H. L. J. Am. Chem. Soc. 1959, 81, 505-506. Corey E. J.; Andersen N. H.; Carlson, R. M.; Paust, J.; Vedejs, E.; Vlattas I.; Winter, R. E. K. J. Am. Chem. Soc. 1968, 90, 3245-3247.
15. Grundmann, C.; Ruske, W. Chem. Ber. 1953, 86, 939-943. Parham, W. E.; Ramp, F. L. J. Am. Chem. Soc. 1951, 73, 1293-1295. Noyce, W. K.; Coleman, C. H.; Barr, J. T. J. Am. Chem. Soc. 1951, 73, 1295-1296. Stilles, M.; Finkbeiner H. L. J. Am. Chem. Soc. 1959, 81, 505-506. Corey E. J.; Andersen N. H.; Carlson, R. M.; Paust, J.; Vedejs, E.; Vlattas I.; Winter, R. E. K. J. Am. Chem. Soc. 1968, 90, 3245-3247.
16. Cundall, R. B.; Locke, A. W. J. Chem. Soc. B 1968, 98-103. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3489-3492. Armand, J. Bull. Soc. Chim. Fr. 1965, 3246-3255.
17. Cundall, R. B.; Locke, A. W. J. Chem. Soc. B 1968, 98-103. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3489-3492. Armand, J. Bull. Soc. Chim. Fr. 1965, 3246-3255.
18. Cundall, R. B.; Locke, A. W. J. Chem. Soc. B 1968, 98-103. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3489-3492. Armand, J. Bull. Soc. Chim. Fr. 1965, 3246-3255.
19. Saville-Stones, E. A.; Lindell, S. D. Synlett 1991, 591-592.
20. Galobardes, M. R.; Pinnick, H. W. Tetrahedron Lett. 1981, 22, 5235-5338.
21. Kornblum, N.; Blackwood, R. K.; Mooberry, D. D. J. Am. Chem. Soc. 1956, 78, 1501-1504.
22. Typical Procedure. A solution of the nitroalkane (1 mmol), sodium nitrite (3 mmol), and acetic acid (10 mmol) in dimethyl sulfoxide (2 mL) was stirred at 35°C for 6 h. After acidification with a 10% aqueous solution of hydrochloric acid, the product was extracted several times with ether and purified by silica gel chromatography.
23. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3483-3488. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3489-3492. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3493-3501.
24. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3483-3488. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3489-3492. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3493-3501.
25. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3483-3488. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3489-3492. Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3493-3501.
26. Meyer V. Ber. 1873, 6, 1492. Wieland, H.; Semper, L. Chem. Ber. 1906, 39, 2522-2526.
27. Meyer V. Ber. 1873, 6, 1492. Wieland, H.; Semper, L. Chem. Ber. 1906, 39, 2522-2526.
28. Brueer, E.; Aurich, H. G.; Nielsen, A. Nitrones, Nitronates & Nitroxides, The chemistry of functional groups; Pataï, S., Ed.; J. Wiley & Sons: New York, 1992.
29. +, 20).
30. Liddell, H. F.; Saville, B. Chem. Ind. 1957, 493-494. Hughes, E. D.; Ingold, C. K.; Ridd, J. H. J. Chem. Soc. 1958, 88-98.
31. Liddell, H. F.; Saville, B. Chem. Ind. 1957, 493-494. Hughes, E. D.; Ingold, C. K.; Ridd, J. H. J. Chem. Soc. 1958, 88-98.