The Synthesis and Diazotization of Some Ketone Hydrazones

Abstract

Hydrazones have been synthesized in this study both from a variety of bicyclic ketones and from ketones containing either the 1-naphthyl or 2-naphthyl group. Three of these hydrazones, those derived from 1-acetonaphthone, 2-acetonaphthone, and benzosuberone, have not been reported previously in the literature. All of the hydrazones were allowed to rearrange in a diazotizing medium to produce amide products. One of these, 4,5-benzoai- heptanolactarn, has never been reported in the literature. From the results of this research, it is possible to reaffirm some general conclusions concerning the utility and scope of the hydrazone diazotization-rearrangement. Among these are the facts that the reaction generally functions well only if at least one aromatic ring is present and that it is stereospecific with migration of the group anti to the NH2 group of the original hydrazone. Thus, the assignment of hydrazone isomer configuration appears to be possible on the basis of the identity of the given amide product. Such assignments have been made for the compounds studied here. Some postulations concerning the steric requirements for hydrazone formation with the aromatic bicyclic ketones have also been made.