Investigation of 2,5-disubstituted silylfurans by PMR spectroscopy

Abstract

The¹H,¹³C, and²⁹Si NMR spectra of S-substituted furfurals and the corresponding diethyl acetals containing various alkylsilyl substituents at position S of the furan ring were studied in comparison with the carbon- and sulfur-containing analogs and also with a series of monosubstituted silylfurans. In cases where the substituent was conjugated with the residue of the furan molecule the effect of the substituent at position S of the furan was transmitted to C_α of the aldehyde group. The reverse effect was also observed. It was determined that the contribution from the aldehyde group and the substituents at position S of the furan to the screening of the carbon nuclei of the furan ring was not additive.