Quinuclidine chemistry: Autocondensation reactions of 3 quinuclidinone

Article abstract of DOI:10.1002/jps.2600660646

During the synthesis of 3-hydroxy-3-ethinylquinuclidine (I), two additional products were isolated and identified as (E)-3-[2-(3-oxoquinuclidine)]quinuclidylidene (III) and (E)-3-[2-(3-hydroxy-3-ethinylquinuclidine)]quinuclidylidene (V). The base-catalyzed auto-condensation of 3-quinuclidinone resulted in the α,β-unsaturated ketone dimer (III) as a single isomer. The geometric configuration was deduced by examination of the NMR spectra of the methyl iodide salt. Compound V was thus the result of attack on the carbonyl carbon of III by the acetylide anion. The isolation and identification of these compounds clarified the reported differences in the physical properties of I and its analogs.