HYDROGEN-BONDING AND THE STEREOCHEMISTRY OF HYDRAZONES AND HYDRAZIDESDERIVED FROM 1,3-DICARBONYL COMPOUNDS INVOLVING IMINO NITROGEN

Beta-Diketones form hydrazones with N',N'-diacylhydrazines and exhibit a six-membered hydrogen bonded cyclic ketiminyl system involving the imino nitrogen. H-1 nmr spectra of the hydrazones obtained from N-amin o -alpha, beta- 9,10-dihydroanthra-cene-9,10-endo-diyl)succinimide and acetylacetone demonstrated restricted rotation about N-N bond and a p laner hydrogen bonded cyclic system orthogonal to the succinimidyl pla ne. Beta-Ketoester behaved differently and reacted in enolic form to g ive intramolecularly hydrogen bonded hydrazide whose stereochemistry h as been established with the help of an asymmetric cage moiety. Both h ydrazones and hydrazides adopt Z-configuration about its olefinic part and the methyl of the ketimino or enamine takes a syn-orientation.