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Reference type: Journal
Authors: Wulff G, Wolf G
Article Title: On the chemistry of binding-sites .6. On the suitability of various aldehydes and ketones as binding-sites for monoalcohols.
Publication date: 1986
Journal: Chemische Berichte-Recueil
Volume: 119
Page numbers: 1876-1889.

Abstract: Suitable binding sites in the chemoselective affinity chromatography should posses a favourable state and a very fast adjustment of the equilibrium with substrates.Aldehydes and ketones of various structure (1-16), from which 3-7 and 10 were prepared for the first time, were investigated for their suitibility to bind monoalcohols via a covalent acetal bond.Especially advantageous were cyclic hemiacetals which showed on acidic catalysis with monoalcohols a fast and reversible formation of acetals.Out of these 1,3-dihydro-1-isobenzofuranol (1a), 1,3-dihydro-7-methoxy-1-isobenzofuranol (5a), and 2H-chromen-2-ol (10) with very fast kinetics seemed to be especially suitable.Acetals of different alcohols were prepared as well and their hydrolytic behaviour was studied.For the preparation of corresponding polymers the polymerizable derivative 20 was synthesized


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