Convenient preparation of deuterated aromatic compounds

Journal Article · Fri Sep 01 04:00:00 EDT 1978 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00412a040· OSTI ID:6477233

Larsen, J W; Chang, L W

The compounds can be prepared by stirring the neat aromatics with a 1:1 molar strong acid system of boron trifluoride: deuterium oxide. Reaction proceeds with polycyclic aromatics and others whose electrophilic reactivity is as great or greater than that of benzene. Compounds deuterated include benzene, toluene, chlorobenzene, toluene, cumene, o-xylene, m-xylene, p-xylene, tertiary-butyl benzene, n-butylbenzene, phenanthrene, naphthalene, and tetralin. The possibility of deuterium incorporation into the aliphatic groups was examined by looking aliphatic C D stretching bands in the ir spectrum. Mass spectra indicated that a mixture of deuterated compounds was present in each reaction product. Extent of deuterium incorporation was measured by comparing the areas of the aromatic and aliphatic NMR peaks in the deuterated products.

• Research Organization: Univ. of Tennessee, Knoxville
• OSTI ID: 6477233
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 43:18; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400303* -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
AROMATICS
BENZENE
BORON COMPOUNDS
BORON FLUORIDES
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
CONDENSED AROMATICS
CUMENE
DEUTERATION
DEUTERIUM
DEUTERIUM COMPOUNDS
FLUORIDES
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HEAVY WATER
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
INFRARED SPECTRA
ISOTOPES
ISOTOPIC EXCHANGE
LIGHT NUCLEI
MAGNETIC RESONANCE
MASS SPECTRA
NAPHTHALENE
NUCLEAR MAGNETIC RESONANCE
NUCLEI
ODD-ODD NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXYGEN COMPOUNDS
PHENANTHRENE
RESONANCE
SPECTRA
STABLE ISOTOPES
SYNTHESIS
TETRALIN
TIME DEPENDENCE
TOLUENE
WATER
XYLENES