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Enantiomerically pure (R)-(+)-2-phenylethanol-2-d and -1,1,2-d/sub 3/, and (S)-(+)-1-phenylethane-1-d, -1,2,-d/sub 2/, -1,2,2-d/sub 3/, and -1,2,2,2-d/sub 4/

Journal Article · · J. Org. Chem.; (United States)
DOI:https://doi.org/10.1021/jo01318a024· OSTI ID:6480050
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(R)-(-)-Mandelic acid has been converted by stereospecific reactions into enantiomerically pure (R)-(+)-2-phenylethanol-2-d (PhCHDCH/sub 2/OH, (..cap alpha..)/sup 20/D +1.52 +- 0.02/sup 0/, neat), (R)-(+)-2-phenylethanol-1,1,2-d/sub 3/ (PhCHDCD/sub 2/OH, (..cap alpha..)/sup 20/D +1.44 +- 0.02/sup 0/, neat), and the four (S)-(+)-deuteriophenylethanes prepared by replacing the hydroxyl groups of these 1-phenylethanols by hydrogen or deuterium. The optical rotation of (S)-(+)-1-phenylethane-1-d (PhCHDCH/sub 3/, (..cap alpha..)/sup 20/D +0.81 +- 0.01/sup 0/, neat) was only slightly different than that of (S)-(+)-1-phenylethane-1,2,2,2-d/sub 4/ (PhCHDCH/sub 3/, (..cap alpha..)/sup 20/D +0.79 +- 0.01/sup 0/, neat), while the corresponding di- and trideuterated analogues had the same rotation within experimental limits ((..cap alpha..)/sup 20/D +0.80 +- 0.01/sup 0/, neat). 4 tables.

Research Organization:
Stanford Univ., California
OSTI ID:
6480050
Journal Information:
J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 44:4; ISSN JOCEA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400302 -- Organic Chemistry-- Isotope Effects-- (-1987)
400303* -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
ALCOHOLS
ALKALI METAL COMPOUNDS
ALUMINIUM COMPOUNDS
ALUMINIUM HYDRIDES
AROMATICS
CARBOXYLIC ACIDS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DATA
DATA FORMS
DEUTERIUM
DEUTERIUM COMPOUNDS
ENANTIOMORPHS
EXPERIMENTAL DATA
HYDRIDES
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY ACIDS
HYDROXY COMPOUNDS
INFORMATION
ISOLATED VALUES
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
LABELLING
LIGHT NUCLEI
LITHIUM COMPOUNDS
LITHIUM HYDRIDES
MANDELIC ACID
MOTION
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ROTATION
STABLE ISOTOPES
YIELDS