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The E-and Z -geometries of the isomeric compounds 4, 6, and 7 were assigned based on the NOESY analysis. NOESY spectra of compounds E-4a, Z-4a, E-4b, Z-4b, Z-4d, Z-4e, Z-4f, Z-6b, and Z-6f are provided in the Supporting Information. The geometries of the other indanes and indanones were determined based on analogy to the above-mentioned compounds. The most characteristic peak is the signal in the 1H NMR spectrum for the proton at the 7-position of the indane/indanone. For the Z -isomers, this signal appears in the regular aromatic region; for the E -isomers, it appears in the range δ 8.5-9.5 ppm. In TLC analyses, the Z-isomers were, consistently, more polar than their E -counterparts.
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If all the reagents are added at the beginning of the reaction, the mixture turns black and neither the Michael nor the Heck reaction occurs.
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