Synthesis and thermal racemization of the 3,4-oxide metabolite of benzo[c] phenanthrene
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1781-1784
- https://doi.org/10.1039/p19840001781
Abstract
Both the racemic form and the (–)-(3R,4S)-enantiomer of benzo[c] phenanthrene 3,4-oxide have been synthesized in 12 steps from naphthalene. The absolute stereochemistry of the arene oxide enantiomers and related chiral derivatives has been determined by n.m.r. methods. Spontaneous thermal racemization of (–)-benzo[c]phenanthrene 3,4-oxide occurred with a barrier to racemization (ΔG≠ 29 °C 24.6 kcal mol–1)(1 kcal = 4.184 kJ) in accord with predictions based upon PMO calculations.This publication has 8 references indexed in Scilit:
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