Optical rotatory dispersion studies. 137. Synthesis and chiroptical properties of. cap alpha. - and. beta. -deuterium substituted aliphatic aldehydes and ketones

Journal Article · Fri May 04 00:00:00 EDT 1984 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00183a007· OSTI ID:6549591

Gorthey, L A; Vairamani, M; Djerassi, C

The synthesis and chiroptical properties of (2R)-2-deuterio-3-hexanone (8a), (2R)-2-deuterio-4-methylpentanone (8b), (2R)-2-deuteriopentanal (9a), (2R)-2-deuterio-3-methylbutanal (9b), and (3R)-3-deuteriohexanal (13) are described. All exhibit Cotton effects consistent with the preferred eclipsed conformation of the carbonyl/..cap alpha..-alkyl moiety. The ..beta..-deuterio aldehyde 13 shows a sign change in accordance with the proximity rule previously observed in CD studies.

• Research Organization: Stanford Univ., CA
• OSTI ID: 6549591
• Journal Information: J. Org. Chem.; (United States), Vol. 49:9
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ALDEHYDES
LABELLING
OPTICAL PROPERTIES
DEUTERIUM
ISOTOPIC EXCHANGE
KETONES
DEUTERIUM COMPOUNDS
EXPERIMENTAL DATA
SYNTHESIS
DATA
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
INFORMATION
ISOTOPES
LIGHT NUCLEI
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
PHYSICAL PROPERTIES
STABLE ISOTOPES
400303* - Organic Chemistry- Isotope Exchange & Isotope Separation- (-1987)