Synthesis of dihalohydrins and tri- and tetra-substituted...

Details Synthesis of dihalohydrins and tri- and tetra-substituted... Synthesis of dihalohydrins and tri- and tetra-substituted...

2006-08-01

2006-08-01

Zucker, Paul A. (Department: 1621)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S438000, C560S047000, C560S104000, C560S128000

Reexamination Certificate

active

07084281

ABSTRACT:
A novel synthesis reaction for highly stereospecific tri- and tetra-substituted olefins is described. A single stereoisomer of stable α-halo-α,β-ester is produced in high yield by the reaction of aldehyde or ketone with a trihalogenated compound such as trichloroacetate in the presence of CrCl2in a solvent. By varying the amount of CrCl2used, the stable dihalohydrin intermediate may be obtained as well.

REFERENCES:
Knochel et al, Tetrahedron, Preparation and Reactivity of Functionalized Alkenyl-Zinc, -Copper, and -Chromium Organometallics, 1993, 49(1), pp. 29-48.
Okazoe et al, Journal of the American Chemical Society, (E)-Selective Olefination of Aldehydes by Means of gem-Dichromium Reagents Derived by Reduction of gem-Diiodoalkanes with Chromium(II) Chloride, 1987, 109, pp. 951 and 953.

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