REISSERT COMPOUNDS

 

            Prof. Gibson has retained an interest in Reissert compounds dating back to his dissertation research.  Although no current students are involved in this area he continues to carry out some research on the  stereochemistry of these compounds.  One example is shown below.  This particular Reissert compound was key to unraveling the complex stereochemistry of this synthetically useful class of compounds using NMR spectroscopy. There is both amide and aryl-carbonyl isomerism, which combine to afford a rich tapestry of stereoisomers observable by NMR.  The accessibility of modern X-ray crystallography has allowed confirmation of the conclusions originally drawn from the NMR studies.

 


 

 

 

 



Two views of one enantiomer from the X-ray crystal structure of 2-(2,6-dimethylbenzoyl)-3-methyl-1,2-dihydroisoquinaldonitrile showing the axial location of the cyano moiety, the trans orientation of the amide linkage and the highly twisted disposition of the aroyl group.