Acid-catalyzed ring-chain tautomerism in 1, 3-diazolidines

JB Lambert, GT Wang, DE Huseland…

Index: Lambert, Joseph B.; Wang, Gen-tai; Huseland, Dave E.; Takiff, Larry C. Journal of Organic Chemistry, 1987 , vol. 52, # 1 p. 68 - 71

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Citation Number: 24

Abstract

Ring-chain tautomerism has been studied in 2-substituted and 1, 3-disubstituted diazolidines. In trifluoroacetic acid, these heterocycles are in equilibrium with the open-chain iminium ion. For materials lacking 2 substitution, &lo% of the chain form is present at room temperature. Because of resonance stabilization of the positive charge, 2-aryl-substituted systems have about 30% of the chain form. All of these ring and chain forms undergo ...