Synthesis and thermal racemization of the predominant arene oxide metabolite of chrysene, (+)-(3S,4R)-chrysene 3,4-oxide
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 595-599
- https://doi.org/10.1039/p19830000595
Abstract
(–)-trans-4-Bromo-3-hydroxy-1,2,3,4-tetrahydrochrysene has been obtained from the chromatographic separation and cleavage of the corresponding menthyloxyacetyl (MOA) diastereoisomer. The (–)-enantiomer of this bromohydrin has been assigned (3R,4R)absolute stereochemistry and used in the synthesis of (+)-(3S,4R)-chrysene 3,4-oxide. Thermal racemization studies on this arene oxide gave a barrier to racemization (Ea) of 25.15 kcal mol–1 and an activation entropy (ΔS‡) of 0.7 cal mol–1 K–1, in accord with PMO predictions.This publication has 2 references indexed in Scilit:
- Biogenesis of epidithiadioxopiperazines. Nucleophilic additions to benzene oxide and sym-oxepin oxideThe Journal of Organic Chemistry, 1982
- Synthesis of (+)- and (–)-naphthalene and anthracene 1,2-oxidesJournal of the Chemical Society, Perkin Transactions 1, 1979