Abstract
The synthesis, isolation, and characterization of new (S )-(+)- and racemic phenylsuccinamic acids, obtained from the reaction of (S )-(+)-phenylsuccinic anhydride (1 ) with five different primary amines (2a -e ) is described. Ring opening of anhydride 1 led to the formation of two isomeric phenylsuccinamic acid products with the phenyl
substituent b to the amide function being the preferred product. Complete racemization
occurred with all of the a-phenylsuccinamic acids (3a -e ) and β-phenylsuccinamic acids 4b and 4c . However, b-phenylsuccinamic acids 4a , 4d , and 4e were found to be optically active.
Key words
anhydride - chirality - nucleophilic addition - racemization - ring opening
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