Synthesis, resolution and racemization studies of 1,2-epoxy-1,2-dihydrochrysene
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1535-1539
- https://doi.org/10.1039/p19820001535
Abstract
(+)-1,2-Epoxy-1,2-dihydrochrysene, a major initial mammalian metabolite of chrysene, has been synthesised and assigned the configuration (1R, 2S). Kinetic studies on the spontaneous thermal racemization of (+)-1,2-epoxy-1,2-dihydrochrysene gave a barrier to racemization (Ea) of 24.8 kcal mol–1. The kinetic results and activation parameters support a thermal racemization mechanism involving an oxepin intermediate.This publication has 8 references indexed in Scilit:
- Metabolism of (−)-trans-(3R,4R)-dihydroxy-3,4-dihydrochrysene to diol epoxides by liver microsomesBiochemical and Biophysical Research Communications, 1981
- METABOLISM OF CHRYSENE AND PHENANTHRENE TO BAY-REGION DIOL EPOXIDES BY RAT-LIVER ENZYMES1981
- Synthesis and absolute stereochemistry of (+)- and (–)-benz[a]anthracene 8,9-oxide and derived mammalian liver metabolites of benz[a]-anthraceneJournal of the Chemical Society, Perkin Transactions 1, 1981
- Racemization of phenanthrene 3,4-oxide. Absolute stereochemistry of cis- and trans-phenanthrene 3,4-dihydrodiolsJournal of the Chemical Society, Perkin Transactions 1, 1981
- An enantiomeric interaction in the metabolism and tumorigenicity of (+)- and (-)-benzo[a]pyrene 7,8-oxide.Journal of Biological Chemistry, 1980
- (+)- and (–)-Benzo[a]pyrene 7,8-oxide : synthesis, absolute stereochemistry, and stereochemical correlation with other mammalian metabolites of benzo[a]pyreneJournal of the Chemical Society, Perkin Transactions 1, 1980
- Absolute stereochemistry of the trans-dihydrodiols formed from benzo[a]anthracene by liver microsomesChemico-Biological Interactions, 1979
- Synthesis of (+)- and (–)-naphthalene and anthracene 1,2-oxidesJournal of the Chemical Society, Perkin Transactions 1, 1979