Ionic hydrogenation of 1-phthaloyl-2-p-substituted benzoylcyclopropanes
1-Phthaloyl-2-p-X-substituted benzoylcyclopropanes (where X=F, Cl, Br, OCH3), regardless of the substituent, are selectively reduced by ionic hydrogenation to 1-phthaloyl-2-p-substituted benzylcyclopropanes. As the electronegativity of the substituent decreases, the reduction rate increases.
The stability of the phthaloyl CO groups and the three-membered ring in this reaction is attributed to their mutual interaction; this agrees well with experimental data and with the13C NMR spectra of the compounds.
KeywordsHydrogenation Experimental Data Rate Increase Reduction Rate Mutual Interaction
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