Selectively deuterated and optically active cyclic ethers
The synthesis of selectively deuterated epihalohydrins (F, Cl, Br, I) and 3,3-bis(chloromethyl)-d/sub 2/)oxetane and some observations on the stereochemistry of each transformation are reported. Further, the synthesis of optically active epihalohydrins, especially the optically active epifluorohydrin, from (S)-glycerol 1,2-acetonide ((S)-2), using mainly KX-18-CR-6 (X = F, Br, I), is reported. This is the first report on the synthesis of optically active epifluorohydrin. The direct halogenation of the presynthesized optically active epichlorohydrin with the same reagents gave the racemized products. The selectively deuterated or optically active compounds reported herein are expected to find a variety of uses in organic chemistry.
- Research Organization:
- Nagoya Univ., Japan
- OSTI ID:
- 6863030
- Journal Information:
- J. Org. Chem.; (United States), Vol. 47:18
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ETHERS
CHEMICAL PREPARATION
HETEROCYCLIC OXYGEN COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
CHEMICAL REACTION KINETICS
DEUTERATION
DEUTERIUM COMPOUNDS
EXPERIMENTAL DATA
CHEMICAL REACTIONS
DATA
HYDROGEN COMPOUNDS
INFORMATION
KINETICS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
REACTION KINETICS
SYNTHESIS
400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)