Selectively deuterated and optically active cyclic ethers

Journal Article · Fri Aug 27 00:00:00 EDT 1982 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00139a049· OSTI ID:6863030

Kawakami, Y; Asai, T; Umeyama, K; Yamashita, Y

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), Journal Name: J. Org. Chem.; (United States) Vol. 47:18; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DATA
DEUTERATION
DEUTERIUM COMPOUNDS
ETHERS
EXPERIMENTAL DATA
HETEROCYCLIC OXYGEN COMPOUNDS
HYDROGEN COMPOUNDS
INFORMATION
KINETICS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
REACTION KINETICS
SYNTHESIS