Abstract

The products of the condensation of 2- (N- phenylhydraz ino)-, 2- (N- p-tolylhydraz ino)-, and 2-(N-p-nitrophen ylhydrazino)etha nols with acetaldehyde, acetone, and pinacone exist in tetrachloroethyl ene solution in the form of tautomeric mixtures of N-aryl-N-(2-hydr oxyethyl)hydrazones and 4-arylperhydro-l ,3,4-oxadiazines . For the case of the pinacone derivatives, it has been shown that the equilibrium concentration of the cyclic form rises with an increase in the electron-accepti ng nature of the substituent in the para position of the aromatic radical. The position of the equilibrium between the tautomeric 4-alkylperhydro- l,3,4-oxadiazine s and the corresponding N-alkyl-N-(2-hyd roxyethyl)hydraz ones depends fundamentally on the spatial requirements of the N-alkyl substituent [2, 3]. Continuing our investigation in this field, we have turned to a study of the structure of derivatives of/3-(N-arylhydr azino) alcohols. Interest in these derivatives was due to the fact that in this case it was possible to determine whether the position of the equilibrium was influenced by the polar effects of substituents on the nitrogen atom, i.e., substituents not bound directly to the reaction center. It is known that in similar ring-chain tautomeric systems - products of the condensation of substituted benzaldehydes of/3- and y-amino alcohols - the equilibrium is shifted in the direction of the cyclic form with a rise in the electron-accepto r capacity of the substituent in the aldehyde fragment [4-6[. 2- (N- Phenylhydrazino) - and 2- (N- p-tolylhydrazino) ethanols (I and lI) were obtained by the nitrosation of 2-(N-arylamino)e thanols [7] followed by the reduction of the nitrosamines with lithium tetrahydroaluminate. The reduction of these compounds with zinc dust in acid [8, 9] or weakly alkaline [10] media

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