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Mitsunobu reaction between hydroxyethyl ether groups and phthalimide is yet another possibility: V. Babain, M. Alyapyshev, M. Karavan, V. Böhmer, L. Wang, E. Shokova, A. Motornaya, I. Vatsouro and V. Kovalev, Radiochirn. Acta, in press.
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note
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A closer look to the chemical shifts for various protons reveals rather strong changes (0.1 ppm or more) with increasing temperature. This may be understood by the assumption that the conformational equilibrium (eqn 1), which is slow on the NMR time-scale is superimposed by a kinetically rapid equilibrium (or equilibria) of one (or both) conformers. Such a rapid equilibrium, e.g. the formation of larger molecular staples, would lead just to an averaged signal for a given proton. Although this interpretation is supported by the observation that dilution of the solution leads to similar chemical shift changes like an increase of the temperature, it remains just an interpretation.
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