Stereoselective epoxidation of cyclic 4-hydroxy olefins

Details Stereoselective epoxidation of cyclic 4-hydroxy olefins Stereoselective epoxidation of cyclic 4-hydroxy olefins

1988-09-20

1990-08-07

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549529, 549531, C07D30114

Patent

active

049469738

ABSTRACT:
The stereoselective expoxidation of cyclic 4-hydroxy olefins is disclosed. These methods involve contacting the cyclic 4-hydroxy olefin with peroxycarboximidic acid, which is preferably generated in situ by contacting an organic nitrile with aqueous hydrogen peroxide. The invention provides unexpectedly high yields of the corresponding cis-epoxides.

REFERENCES:
patent: 3053856 (1962-09-01), Payne et al.
R. G. Carlson, et al., J. Org. Chem., "Epoxidation," 36, pp. 3832-3833, (1971).
C. H. Gragnieu, et al., J. Chem. Soc. Perkin I, "A New Procedure for Olefin Oxiranation by Peroxybenzimidic Acid" . . . , pp. 1009-1011, (1982).
F. A. Corey and R. J. Sundberg, "Advanced Organic Chemistry," 2nd ed., pp. 494-498, Plenum Press, New York (1983).
Chemical Abstracts 107: 154227a, Abstract of Japanese Patent 62-114,979.
Achmatowicz and Szechner, Carbohydrate Res., 50, pp. 23-33, (1976).

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