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Issue 1, 2007
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A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles

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Abstract

Functionalized 2-formylphenylboronic acids undergo an unprecedented tautomeric rearrangement in solution to form corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles. X-Ray analyses of selected examples revealed diverse solid-state molecular structures from a planar open form with a hydrogen-bonded carbonyl group (X = 3-F) through a twisted conformer showing a weak carbonyl–boron interaction (X = 3,5-Br2) to a cyclic oxaborole derivative (X = 3-Br). Variable-temperature 1H NMR spectroscopy was used to determine equilibrium constants as well as enthalpies and entropies of tautomerization in a mixed solvent [D6]acetoneD2O (95 : 5). A computational approach to the process by DFT (B3LYP) and MP2 methods has also been performed.

Graphical abstract: A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles

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Article information


Submitted
02 Aug 2006
Accepted
09 Nov 2006
First published
06 Dec 2006

New J. Chem., 2007,31, 144-154
Article type
Paper

A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles

S. Luliński, I. Madura, J. Serwatowski, H. Szatyłowicz and J. Zachara, New J. Chem., 2007, 31, 144
DOI: 10.1039/B611195E

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