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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 29, 1999 - Issue 22
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Original Articles

Selective Chlorination of Hydroxynaphthazarins with Dichlorine Monoxide. Remarkable Stability of some Geminal Diols Derived from 2,3-Dihydro-2-oxonaphthazarin

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Pages 3971-3980 | Received 04 Nov 1998, Published online: 17 Sep 2007

References

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  • Thapliyal , P. C. , Singh , K. P. and Khanna , R. N. 1994 . Synth. Commun. , 24 : 1079
  • Anufriev , V. Ph. , Novikov , V. L. , Maximov , O. B. , Elyakov , G. B. , Levitsky , D. O. , Lebedev , A. V. , Sadretdinov , S. M. , Shvilkin , A. V. , Afonskaya , N. I. , Ruda , M. Ya. and Cherpachenko , N. M. 1998 . BioMed Chem. Lett. , 8 : 587
  • Gubrie , Z. V. , Klep , V. Z. , Litvin , B. L. and Novikov , V. P. 1996 . Zh. Org. Khim. , 32 : 948 In Russian
  • Anufriev , Ph V. , Malinovskaya , G. V. , Novikov , V. L. , Balanyova , N. N. and Polonik , S. G. 1998 . Synth. Commun. , 28 : 2149
  • Anufriev , V. Ph. , Tchizhova , A. Ya. , Denisenko , V. A. and Novikov , V. L. 1993 . Zh. Org. Khim. , 29 : 2008 In Russian
  • Huber , F. and Schmeisser , M. 1975 . in Handbuch der Praparativen Anorganischen Chemie , Edited by: Brauer , G. Stuttgart : Ferdinand Enke Verlag .
  • For all IR spectra: strong, vs very strong, m middle, w weak, vw very weak, br broad.
  • In the IR spectra of compounds 3a, 9b, and 9c the bands of stretching vibration of a-OH groups shift below 3000 cm -1, become more broad and so they are difficult to observe
  • IR and 1 H NMR spectra of compounds 8a-c were obtained using dry solvents
  • In the IR and 1H NMR spectra of gem-diols 9a-c in CD Cl3 and CDCl3 the proton signals of corresponding oxo derivatives 8a-c were observed
  • Owing to relative lability the sharp melting points and satisfactory elemental analysis of gem-diols 9a-c were not obtained

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