An improved procedure for the preparation of the O,2-dianion of allyl alcohol

Synthetic Communications

Volumn 27, Issue 12, 1997, Pages 2111-2115

  Hegde, Sayee G ^a   Myles, David C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOPROPEN 1 OL; ALLYL ALCOHOL; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; HALOGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS;

EID: 0030907647     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006818     Document Type: Article

References (18)

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2. (a) Schmidt, U.; Schmidt, J. Synthesis, 1994, 300.
3. (b) Schmidt, U.; Schmidt, J. J. Chem. Soc., Chem. Commun., 1992, 529.
4. (c) Tanaka, A.; Kamata, H.; Yamashita, K. Agric. Biol. Chem., 1988, 52, 2043.
5. (d) Cuomo, J. J. Agric. Food Chem., 1985, 33, 717.
6. (e) Gao, Y.; Iijima, S.; Urabe, H.; Sato, F. Inorganica Chimica Acta, 1994, 222, 145.
7. For related dianions, see (a) Still, W. C.; McDonald, J. H. III; Collum, D. B.; Mitra, A. Tetrahedron Letters, 1979, 20, 593. (b) Semmelhack, M. F.; Kim, C. R.; Dobler, W.; Meier, M. Tetrahedron Letters, 1989, 30, 4925. (c) Barrett, A. G. M.; Barta, T. E.; Flygare, J. A. J. Org. Chem., 1989, 54, 4246.
8. For related dianions, see (a) Still, W. C.; McDonald, J. H. III; Collum, D. B.; Mitra, A. Tetrahedron Letters, 1979, 20, 593. (b) Semmelhack, M. F.; Kim, C. R.; Dobler, W.; Meier, M. Tetrahedron Letters, 1989, 30, 4925. (c) Barrett, A. G. M.; Barta, T. E.; Flygare, J. A. J. Org. Chem., 1989, 54, 4246.
9. For related dianions, see (a) Still, W. C.; McDonald, J. H. III; Collum, D. B.; Mitra, A. Tetrahedron Letters, 1979, 20, 593. (b) Semmelhack, M. F.; Kim, C. R.; Dobler, W.; Meier, M. Tetrahedron Letters, 1989, 30, 4925. (c) Barrett, A. G. M.; Barta, T. E.; Flygare, J. A. J. Org. Chem., 1989, 54, 4246.
10. (a) Nishiyama, H.; Yokoyama, H.; Narimatsu, S.; Itoh, K. Tetrahedron Letters, 1982, 23, 1267.
11. (b) Kitamura, M.; Nagai, K.; Hsiao, Y.; Noyori, R. Tetrahedron Letters, 1990, 31, 549.
12. (c) Barluenga, J.; Fernandez, J. R.; Yus, M. J. Chem. Soc. Perkin. Trans. I, 1985, 447.
13. 2-bromopropen-1-ol was prepared from 2,3-dibromopropene in 75% yield following a published procedure. See Hutchins, R. O.; Taffer, I. M. J. Org. Chem., 1983, 48, 1360.
14. Similar directed elimination reactions have been reported: (a) Suffert, J.; Toussaint, D. J. Org. Chem., 1995, 60, 3550.
15. (b) Bonnet, B.; Plé, G.; Duhamel, L. Synlett, 1996, 221.
16. (c) Barluenga, J.; Canteli, R. M.; Flórez, J. J. Org. Chem., 1996, 61, 3646.
17. (d) Meyers, A. I.; Spohn, R. F. J. Org. Chem. 1985, 50, 4872.
18. Hegde, S. G.; Myles, D. C. * Presented at the 212th National Meeting of the American Chemical Society, Orlando, FL, August 1996; paper number ORGN 125.