Potentially carcinogenic cyclopenta[a]phenanthrenes (1,2-cyclopentenophenanthrenes). Part II. Derivatives containing further unsaturation in ring D
- 1 January 1966
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- Vol. 10, 963-968
- https://doi.org/10.1039/j39660000963
Abstract
Substituted 17-methyl-15H-cyclopenta[a]phenanthrenes have been prepared from the corresponding 15,16-dihydro-17-ketones by the Grignard reaction, and reduced to the analogues of the Diels hydrocarbon. The 15,16-dihydro-17-methylene-derivative (unsubstituted) was obtained by the Witting reaction. Elimination from the 17-toluene-p-sulphonyloxy-compound at 170° gave the Δ15– 17H-compound (A), but at 100° the Δ16– 15H-isomer was formed. Base-catalysed condensation of (A) with acetone and aryl aldehydes yielded 17-substituted-methylene derivatives. The chemical shifts of protones attached to ring D in these compounds are listed.Keywords
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