H/D exchange in electrolytic reduction reactions of phenyl ketones

Journal Article · Wed Sep 14 04:00:00 EDT 1977 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00461a024· OSTI ID:7285851

Diaz, A F; Cheng, Y Y; Ochoa, M

Reduction of phenacyl chloride in DMF containing 1 percent D/sub 2/O is electrochemically irreversible. The observed products at the reduction potential are acetophenone plus dimeric product. Recovery of the ketone after short reaction times reveals the presence of considerable H/D exchange of the methylene hydrogens in competition with the reduction reaction. Similarly, in the reduction of 1,2-diphenylpropanone, which proceeds with asymmetric induction, H/D exchange of the ..cap alpha.. hydrogen is very important. The exchange process appears to be part of the electrochemical reaction and is associated with the first electron transfer step.

• Research Organization: IBM Research Lab., San Jose, CA
• OSTI ID: 7285851
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 99:19; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400303* -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
DEUTERIUM
ELECTROLYSIS
HYDROGEN ISOTOPES
ISOTOPES
ISOTOPIC EXCHANGE
KETONES
LIGHT NUCLEI
LYSIS
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
STABLE ISOTOPES