A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles
New Journal of Chemistry, ISSN: 1369-9261, Vol: 31, Issue: 1, Page: 144-154
2007
- 53Citations
- 43Captures
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Article Description
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-Br) to a cyclic oxaborole derivative (X = 3-Br). Variable-temperature H NMR spectroscopy was used to determine equilibrium constants as well as enthalpies and entropies of tautomerization in a mixed solvent [D]acetone-DO (95:5). A computational approach to the process by DFT (B3LYP) and MP2 methods has also been performed. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=33846009425&origin=inward; http://dx.doi.org/10.1039/b611195e; https://xlink.rsc.org/?DOI=B611195E; http://xlink.rsc.org/?DOI=B611195E; http://pubs.rsc.org/en/content/articlepdf/2007/NJ/B611195E; https://dx.doi.org/10.1039/b611195e; https://pubs.rsc.org/en/content/articlelanding/2007/nj/b611195e
Royal Society of Chemistry (RSC)
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