An improved preparation of 3-bromo-2H-pyran-2-one: An ambiphilic diene for diels-alder cycloadditions: [2H-Pyran-2-one, 3-bromo-]

Organic Syntheses

Volumn 73, Issue , 1996, Pages 231-

  Posner, G H ^b   Afarinkia, K ^b   Dai, H ^a   Guevel, Alyx Caroline ^b   Hart, David J ^b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85027879301     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.073.0231     Document Type: Article

References (12)

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2. Bock, K.; Pedersen, C.; Rasmussen, P. Acta Chem. Scan. 1975, 29B, 389.
3. Pirkle, W. H.; Dines, M. J. Heterocyclic Chem. 1969, 6, 1.
4. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. "Purification of Laboratory Chemicals," 2nd ed.; Pergamon Press: New York, 1980.
5. Nakagawa, M.; Saegusa, J.; Tonozuka, M.; Obi, M.; Kiuchi, M.; Hino, T.; Ban, Y. Org. Synth., Coll. Vol. VI 1988 462.
6. Posner, G. H.; Harrison, W.; Wettlaufer, D. G. J. Org. Chem. 1985, 50, 5041;
7. Posner, G. H.; Nelson, T. D.; Kinter, C. K.; Johnson, N. J. Org. Chem. 1992, 57, 4083.
8. Posner, G. H.; Nelson, T. D.; Kinter, C. M.; Afarinkia, K. Tetrahedron Lett. 1991, 32, 5295;
9. For a review of 2-pyrone cycloadditions see: Afarinkia, K.; Vinader, M. V.; Nelson, T. D.; Posner, G. H. Tetrahedron Report 1992, 48, 9111;
10. For applications to synthesis of vitamin D3 analogs, see Posner, G. H.; Dai, H. BioMed. Chem. Lett., 1993, 3 1829;
11. For cycloadditions using 5-bromo-2-pyrone, see Afarinkia, K.; Posner, G. H. Tetrahedron Lett. 1992, 33, 7839;
12. For an improved procedure for preparation of 3-bromo-2-pyrone, see Posner, G. H.; Lee, J. K.; White, M. C.; Hutchings, R. H.; Dai, H.; Kachinski, J. L.; Dolan, P.; Kensler, T. W. J. Org. Chem. 1997, 62, 3299.