The determination of the relative geometry of substituents on the 5-membered indanone ring and the corresponding indanol derivatives involved the utilization of deuterium substitution, spin-spin decoupling, and the calculation of the theoretical spectra wherever applicable. The NMR spectra of a series of methylsubstituted 1-indanones and indanols were obtained and the stereochemistry was determined. The coupling constants were used as a criterion for the conformation of the 5-membered ring. Spin-spin decoupling experiments were used for further confirmation of the assignment of the ring protons. Theoretical spectra were obtained for the 2-and 3-methyl-l-indanones.The data indicate that the ring geometry and symmetry is dependent on the nature and the number of the substituents on the 5-membered ring.The preparation of indanone and indanone derivatives usually involves a series of reactions; however, the novel synthesis reported (J) has made possible a study of substituted 1indanones by proton nuclear magnetic resonance spectrometry. The elimination reactions of 2-bromo-2(a-bromobenzyl)-l-indanones and 2-bromo-2(a-bromobenzyl)-3,3 -dimethyl-1 -indanone have been studied, and infrared and ultraviolet spectral data were obtained (2). Elvidge and Foster (3) published nuclear magnetic spectral data for a series of indenes, whose structures were established by means of the proton resonance spectra of parent indanones and indanols. These authors demonstrated the presence of long range proton coupling in the series of indenes studied. Related work on 2-substituted indanes (4) has been reported. These authors utilized the formation of the indane complex with tricarbonyl chromium to obtain data concerning the geometry of the indane 5-membered ring. Recently, the NMR spectra of 1,2disubstituted indanes and related indanones have been obtained and the data reported by Rosen, Dorfman, and Linfield (5). Their discussions involved the dependence of the coupling constants of the protons of the 5-membered ring on ring planarity. However, a study of a series of 1-indanones has not been the subject of reported data thus far.The scope of this study includes the determination of the relative geometry of indanones and the corresponding indanol derivatives, as well as a discussion of interesting phenomena encountered. The stereochemistry of the compounds that were studied was determined by conversion of the indanones to indanols with sodium borohydride and by consideration of the
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