The influence of homoconjugation in bicyclic aldehydes was studied by observing the formation of cis and trans isomers in enamines. Homoconjugation has been the reason for forming enamines and teriary amines that otherwise would not form (A. Cook). Pyrrolidine, piperidine, morpholine, 5-norbornene-2-carboxaldehyde and norbornane 2-carboxaldehyde were the amines and aldehydes used in the study, respectively. Cis and trans isomers were yielded in reactions with 5-norbornene-2-carboxaldehyde and each amine; cis and trans isomers were also formed in the reactions with norbornane-2-carboxaldehyde and each amine. When present, homoconjugation in the bicyclic aldehyde changed the cis to trans isomer ratio in the enamine due to its stabilization properties.
Borchert, Michael, "Homoconjugation in the Synthesis of Bicyclic Enamines" (2011). Symposium on Undergraduate Research and Creative Expression (SOURCE). 66.