13C NMR Shifts and Conformations of Substituted Indans

Article abstract of DOI:10.1002/omr.1270210215

13C NMR spectra of indan derivatives bearing substituents in the 1,2,5 and 6 positions are reported and assigned by LIS measurements and other techniques.Epimeric indanes bearing vicinal oxygen and phenyl or benzyl susbtituents show ring carbon shielding in the cis relative to the trans isomers, which is compared with corresponding cyclopentane shifts, and indicates the predominance of envelope confomations with pseudoaxial oxygen substituents for the cis isomers.Acetylation shifts show consistently larger shielding at pseudoaxial oxygen substituents for the cis isomers.Acetylation shifts show consistently larger shielding at C-β for the trans compounds.Introduction of oxygen at C-5 leads to asymmetric shielding effects at the ortho carbon atoms as soon as there is a substituent in the para position which can participate in mesomeric forms.