Allene epoxidation: Synthesis of functionalized lactones by the DMDO oxidation of allenic acids

Tetrahedron

Volumn 58, Issue 35, 2002, Pages 7027-7036

  Crandall, Jack K ^a   Rambo, Elisa ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Allenic acids; Dimethyldioxirane; Epoxidation of allenes; Lactone synthesis

Indexed keywords

ACID; ALLENE DERIVATIVE; DIMETHYLDIOXIRANE; KETOL; LACTONE DERIVATIVE; OXIDE; OXIDIZING AGENT; SPIRO COMPOUND;

ARTICLE; CYCLIZATION; EPOXIDATION; METHODOLOGY; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0037178958     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00698-1     Document Type: Article

References (24)

1. Stang P.J. In The Chemistry of Functional Groups, Supplement E. The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and their Sulphur Analogues; Patai, S., Ed.; Wiley New York: 1980; pp 859-879
2. (a) Stang P.J. Patai S., The Chemistry of Functional Groups, Supplement E. The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and their Sulphur Analogues. 1980;859-879 Wiley, New York, (b) Chan T.H., Ong B.S. Tetrahedron. 36:1980;2269-2289.
3. Crandall J.K., Machleder W.H. Tetrahedron Lett. 1966;6037-6041.
4. Crandall J.K., Machleder W.H., Sojka S.A. J. Org. Chem. 38:1973;1149-1154.
5. Camp R.L., Greene F.D. J. Am. Chem. Soc. 90:1968;7349.
6. Crandall J.K., Conover W.W., Komin J.B., Machleder W.H. J. Org. Chem. 39:1974;1723-1729.
7. Crandall J.K., Machleder W.H. J. Am. Chem. Soc. 90:1968;7347-7349.
8. Crandall J.K., Machleder W.H., Thomas M.J. J. Am. Chem. Soc. 90:1968;7346-7347.
9. Murray R.W., Jeyaraman R. J. Org. Chem. 50:1985;2847-2853.
10. Crandall J.K., Batal D.J., Sebesta D.P., Lin F. J. Org. Chem. 56:1991;1153-1166.
11. Baumstark A.L.; McCloskey C.J. Tetrahedron Lett. 1987, 28, 3311-3314.
12. (a) Baumstark A.L., McCloskey C.J. Tetrahedron Lett. 28:1987;3311-3314 (b) Baumstark A.L., Vasquez P.C. J. Org. Chem. 53:1988;3437-3439.
13. Crandall J.K., Batal D.J., Lin F., Reix T., Nadol G.S., Ng R.A. Tetrahedron. 48:1992;1427-1448.
14. Bertrand M.; Dulcere J.P.; Gil G. Tetrahedron Lett. 1980, 21, 1945-1948.
15. Bertrand M.; Dulcere J.P.; Gil G. Tetrahedron Lett. 1977, 18, 3807-3810.
16. Bertrand M., Dulcere J.P., Gil G. Tetrahedron Lett. 21:1980;1945-1948 Bertrand M., Dulcere J.P., Gil G. Tetrahedron Lett. 18:1977;3807-3810 Bertrand M., Dulcere J.P., Gil G., Grimaldi J., Sylvestre-Panthet P. Tetrahedron Lett. 17:1976;3305-3308.
17. . For a preliminary publication, see: Crandall J.K., Rambo E. J. Org. Chem. 55:1990;5929-5930.
18. PCMODEL v7.5; Serena Software, Box 3076, Bloomington, IN 47402-3076.
19. Crandall J.K., Reix T. Tetrahedron Lett. 35:1994;2513-2516.
20. Kirby A. J. Adv. Phys. Org. Chem. 17:1980;183-278.
21. Crandall J.K., Rambo E. Tetrahedron Lett. 35:1994;1489-1492.
22. Kolsaker P., Boerresen S. Acta Chem. Scand., Ser. B33:1979;133-137.
23. Hoff S., Brandsma L., Arens J.F. Rec. Trav. Chim. 87:1968;159-161.
24. Jensen J.E., Torssell K. Acta Chem. Scand., Ser. B32:1978;457-459.