Ionic hydrogenation of 1-phthaloyl-2-p-substituted benzoylcyclopropanes
- 14 Downloads
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
Unable to display preview. Download preview PDF.
- 1.D. N. Kursanov, Z. N. Parnes, M. I. Kalinkin, and N. M. Loim, Ionic Hydrogenation [in Russian], Khimiya, Moscow (1979).Google Scholar
- 2.O. K. Popova, N. I. Kopteva, L. P. Zalukaev, S. M. Markosyan, M. I. Kalinkin, Z. N. Parnes, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Ser. Khim., 2084 (1981)Google Scholar
- 3.N. A. Revina, S. I. Belykh, L. P. Zalukaev, Z. N. Parnes, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Ser. Khim., 2003 (1980).Google Scholar
- 4.L. F. Johnson and W. C. Jankowski, Carbon 13 NMR Spectra, Wiley-Interscience, New York (1972).Google Scholar
- 5.E. Breitmeier, G. Haus, and W. Voelter, Atlas of Carbon NMR Data, London (1973).Google Scholar
- 6.J. B. Stothers, Carbon 13 NMR Spectroscopy, Academic Press, New York (1972).Google Scholar
- 7.I. K. Anokhina and N. V. Remizova, VINITI Deposit, No. 1746 (1975).Google Scholar
- 8.N. M. Loim, V. A. Baranova, L. V. Moiseeva, L. P. Zalukaev, Z. N. Parnes, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Ser. Khim., 843 (1974).Google Scholar