Nitroalkanes as a new source of 2-alkylidene-1,4-diols, in two steps

Tetrahedron

Volumn 55, Issue 47, 1999, Pages 13451-13456

  Ballini, Roberto ^a   Bosica, Giovanna ^a   Damiani, Marco ^a   Righi, Paolo ^b  

^a Dipto Scienze Chimiche dell'Univ   (Italy)

^b Dipto di Chimica Organica   (Italy)

Author keywords

Diols; Elimination; Michael reaction; Nitro compounds; Nitrous acid

Indexed keywords

ALKANE DERIVATIVE; NITROALKANE; NITROUS ACID;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROXYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033585133     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00829-7     Document Type: Article

References (26)

1. (a) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; John Wiley and Sons: New York, 1989.
2. (b) Lindberg, T. Strategies and Tactics in Organic Synthesis; Academic Press, Inc.: San Diego, 1994, vol. 1.
3. (c) Ho, T. L. Tactics of Organic Synthesis; John Wiley and Sons: New York, 1994.
4. (a) Fetizon, M.; Golfier, M.; Louis, J. M. Tetrahedron 1975, 31, 171-176.
5. (b) Jefford, C. W.; Wang, Y. J. Chem. Soc., Chem. Commun. 1988, 634-635.
6. (c) Boekman Jr, R. K.; Thomas, E. W. Tetrahedron Lett. 1976, 17, 4045-4048.
7. (d) Kretchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379-3380.
8. (e) Lansbury, R. T.; Hangauer Jr, Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964-3965.
9. (f) Tamara, Y.; Yamada, Y.; Inove, K.; Yamamoto, Y.; Yoshida, Z. J. Org. Chem. 1983, 48, 1286-1292.
10. (g) Murahashi, S.-I.; Naota, T.; Ito, K.; Maeda, Y.; Taki, H. J. Org. Chem. 1987, 52, 4319-4327.
11. (h) Ishii, Y.; Suzuki, K.; Ikariya, T.; Sabari, M.; Yoshikawa, S. J. Org. Chem. 1986, 51, 2822-2824.
12. (i) Doyle, M. P.; Dow, R. L.; Bagheri, V.; Patrie, W. J.; Yoshida, Z. J. Org. Chem. 1983, 48, 476-480;.
13. (j) Jung, M. E.; Brown, R. W. Tetrahedron Lett. 1978, 19, 2771-2774.
14. (k) Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659-4665.
15. (l) Lok, K. P.; Jakovac, I. J.; Jones, J. B. J. Am. Chem. Soc. 1985, 107, 2521-2526.
16. Comprehensive Organic Functional Group Transformations; Katrinsky, A. R.; Meth-Cohn, O.; Rees, C. V., Eds; Pergamon Press: Oxford, 1995, vol. 6.
17. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991.
18. (a) Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1-18.
19. (b) Rosini, G.; Ballini, R. Synthesis 1988, 833-847.
20. (c) Ballini, R. In Studies in Natural Products Chemistry; Atta-ur-Rahman Ed.; Elsevier: Amsterdam, 1997, vol 19, pag. 117-184.
21. (a) Ballini, R.; Marcantoni, E.; Perella, S. J. Org. Chem. 1999, 64, 2954-2957.
22. (b) Ballini, R.; Petrini, M. Tetrahedron Lett. 1999, 40, 4449-4452.
23. Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans 1 1999, 749-764.
24. Dieter, D. K.; Silks III, L. A.; Fishpaugh, J. R.; Kastner, M. E. J. Am. Chem. Soc. 1985, 107, 4679-4692.
25. Ballini, R.; Bosica, G. J. Chem. Res. (S) 1993, 371.
26. Ballini, R.; Petrini, M.; Rosini, G. Tetrahedron 1990, 46, 7531-7538.