Abstract
The stereochemical features of the reaction between 4-nitrophenyl azide and some enamines deriving from straight-chain aliphatic ketones or aryl alkyl ketones have been studied. Under kinetically controlled conditions the cis–trans equilibrium mixture of the enamine reacts with the azide, yielding exclusively the trans-triazoline. At higher temperature or in the presence of acidic catalysts, the trans-triazoline epimerizes, thus affording a cis–trans equilibrium mixture. The factors which affect the equilibrium position and the epimerization rate are discussed and a probable epimerization mechanism is suggested.
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More From: Journal of the Chemical Society, Perkin Transactions 1
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