STEREOCHEMISTRY OF CAMPHOR HYDRAZONE AND ITS DERIVATIVES - H-1 AND C-13 NMR SPECTRAL STUDIES

(+/-)-Camphor forms hydrazone with an excess of hydrazine hydrate in m ethanol and its stereochemistry has been shown to be anti; (4) on the basis of anisotropic interaction of the sp(2)-nitrogen on the 10-methy l and 3-methylene groups. Its mono- and di-acetyl derivatives have bee n assigned anti-configuration. The diacetyl derivative on heating in x ylene is transformed into an isomeric product. These compounds have be en proposed to be stable rotamers about the N-N bond with trans-arrang ement of N'-carbonyls. C-13 NMR has been shown to be quite diagnostic in the stereochemical assignment. The tosyl derivative exhibits a stro ng anisotropic shielding on the 10-methyl and has been assigned syn-co nfiguration (5).