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Reference type: Journal
Authors: Lauer M, Böhnke H, Grotstollen R, Salehnia M, Wulff G
Article Title: On the chemistry of binding-sites, 4. On an unusual increase in reactivity of arylboronic acids by neighboring groups.
Publication date: 1985
Journal: Chemische Berichte-Recueil
Volume: 118
Page numbers: 246-260.

Abstract: ortho-Substituted arylboronic acids were investigated for subsequent use as binding sites.The introduction of different aminomethyl groupings resulted in a strong acceleration of the adjustment of the equilibrium of the esterification with diols as well as the transesterification of such esters.The rate of the transesterification was investigated with suitable systems by dynamic NMR spectroscopy.According to an estimation the enhancement compared with the unsubstituted compound amounted to 8 orders of magnitude.Most of the compounds showed a strong B-N-coordination as was shown by 11B NMR.There proved, however, to be no simple relation between B-N-coordination and the catalytic activity of the neighbouring groups.Neighbouring groups containing oxygen, sulfur, and fluorine showed no enhancement of esterification or transesterification and no coordination with the boron


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