An imidazolidin-1-ol, nitrone and oxadiazinane ring-chain-ring tautomeric dynamic combinatorial library

Coskun N. , Aksoy C.

TETRAHEDRON LETTERS, vol.50, no.25, pp.3008-3012, 2009 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 50 Issue: 25
  • Publication Date: 2009
  • Doi Number: 10.1016/j.tetlet.2009.03.201
  • Title of Journal : TETRAHEDRON LETTERS
  • Page Numbers: pp.3008-3012


A dynamic combinatorial library (DCL) based on benzylidene exchange reactions between imidazolidin-1-ol, nitrone and oxadiazinane (INO) ring-chain-ring tautomers at room temperature is created. The probable mechanism of the reaction is discussed based on Hammett type correlation analyses. The equilibria in the DCL are defined as interconversion of INOAr-X to INOAr-Y as a result of reactions with the corresponding aldehydes Y-ArCHO and X-ArCHO and are shown to depend on the sigma constants of the substituents and are described by a simple equation logK(XY) = rho sigma(dif) + logK(XY)(x = y). The prediction of K(XY) for any INOAr-X and INOAr-Y interconversion requires only the experimental values of rho and the known Hammett sigma constants of the substituents. The effect of Zn(II) and CF(3)SO(3)H on the DCL equilibria is also reported. (C) 2009 Elsevier Ltd. All rights reserved.