Stereochemistry of ethynylation, normant, and grignard reactions in the 1-alkyldecahydro-4-quinolone series

IR Spectroscopic Investigation and Conformational Analysis of Unsaturated C20 and C22 Steroid Alcohols

“…1) is related to the absorption of the hydroxyl groups incorporated into the intramolecular hydrogen bond. A similar shift of the ν(OH) band was observed by us earlier [25,26] in the spectra of decahydroquinoline alcohols on incorporation of the OH groups into the intramolecular hydrogen bond with an unshared electron pair of nitrogen atoms. At the same time, with the same distance between the interacting OH group and C=C bond in the conformer a 3 B of tertiary alcohol 2 and conformer a 2 B of secondary alcohol 4, in the spectrum of the latter a shift of the band that is half as large and is caused by the formation of the intramolecular hydrogen bond is attained, which can be explained by the different stability of the resulting single-bridge intrachelate cycles of different magnitude [27].…”