Reactions of the K-region epoxides of polycyclic aromatic hydrocarbons with phosphodiesters. A potential detoxification reaction

Journal Article · Fri Apr 09 00:00:00 EST 1982 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00347a009· OSTI ID:6847188

Di Raddo, P; Chan, T H

Phenanthrene 9,10-oxide reacts with diethyl hydrogen phosphate to give 9-phenanthrol. The reaction was first, order in both epoxide and phosphate concentrations, with a pseudo-first-order rate constant k/sub psi/ = 6.2 x 10/sup -1/ mol/sup -1/ L s/sup -1/. Similarly, chrysene 5,6-oxide on reaction with phosphate opened regiospecifically to give 6-chrysenol. Several anilinium phosphate salts were prepared and reacted with phenanthrene 9,10-oxide. The extent of reaction was markedly influenced by the pK/sub a/ of the anilinium salt. The biological implications of the study in understanding the relative noncarcinogenicity of K-region arene oxides are discussed.

• Research Organization: McGill Univ., Montreal, Canada
• OSTI ID: 6847188
• Journal Information: J. Org. Chem.; (United States), Vol. 47:8
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
59 BASIC BIOLOGICAL SCIENCES
01 COAL, LIGNITE, AND PEAT
CHRYSENE
CHEMICAL REACTIONS
DETOXIFICATION
PHENANTHRENE
PHOSPHATES
CARCINOGENS
CHEMICAL REACTION KINETICS
EPOXIDES
EXPERIMENTAL DATA
SPECTRA
AROMATICS
CONDENSED AROMATICS
DATA
HYDROCARBONS
INFORMATION
KINETICS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXYGEN COMPOUNDS
PHOSPHORUS COMPOUNDS
REACTION KINETICS
400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)
550500 - Metabolism
010500 - Coal
Lignite
& Peat- Products & By-Products