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Macrocyclization of the semiclathrochelate o-carboranylboronate and n-butylboronate iron(II) oximehydrazonates: synthesis and structure of clathrochelate products and unexpected allosteric effect of the apical substituent

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Abstract

The template condensation of diacetylmonooxime hydrazone (HDXO) with n-butylboronic acid and dimethyl ester of o-carboranyldiboronic acid on the iron(II) ion matrix afforded the [Fe(DXO)3(BBu)](BF4) and [Fe(DXO)3(Bo-carb)](BF4) semiclathrochelates. The H+-ion-catalyzed macrocyclization of these precursors with an excess of formaldehyde and triethyl orthoformate (TOF) resulted in the corresponding macrobicyclic complexes. In the case of o-carboranylboronate semiclathrochelate, the macrocyclization with TOF gave the clathrochelate with the previously unknown syn,syn,anti-orientation of the ethoxy substituents relative to the 1,3,5-triazacyclohexane capping fragment. The complexes obtained were characterized using elemental analysis, IR, UV-Vis, MALDI-TOF mass, 1H, 11B, and 13C NMR, and 57Fe Mössbauer spectroscopies and X-ray crystallography.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    Ya. Z. Voloshin, I. G. Makarenko, E. G. Lebed’, Z. A. Starikova & Yu. N. Bubnov

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    S. Yu. Erdyakov, T. V. Potapova, S. V. Svidlov, M. E. Gurskii & Yu. N. Bubnov

  3. Institute of Metallophysics, National Academy of Sciences of Ukraine, 36 bulv. Vernadskogo, 03680, Kiev-142, Ukraine

    E. V. Pol’shin

Authors
  1. Ya. Z. Voloshin
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  2. S. Yu. Erdyakov
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  3. I. G. Makarenko
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  4. E. G. Lebed’
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  5. T. V. Potapova
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  6. S. V. Svidlov
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  7. Z. A. Starikova
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  8. E. V. Pol’shin
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  9. M. E. Gurskii
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  10. Yu. N. Bubnov
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Corresponding author

Correspondence to Ya. Z. Voloshin.

Additional information

Dedicated to Academician G. A. Abakumov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1724–1731, September, 2007.

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Voloshin, Y.Z., Erdyakov, S.Y., Makarenko, I.G. et al. Macrocyclization of the semiclathrochelate o-carboranylboronate and n-butylboronate iron(II) oximehydrazonates: synthesis and structure of clathrochelate products and unexpected allosteric effect of the apical substituent. Russ Chem Bull 56, 1787–1794 (2007). https://doi.org/10.1007/s11172-007-0278-7

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  • DOI: https://doi.org/10.1007/s11172-007-0278-7

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