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Synthesis of formyl derivatives of benzodiazacrown ethers and benzocryptands

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Russian Chemical Bulletin Aims and scope

Abstract

A simple and convenient procedure was developed for the synthesis of formyl derivatives of benzodiazacrown ethers and benzocryptands by condensation of 3,4-bis(2-iodoethoxy)benzaldehyde with α,ω-oligooxaalkanediamines or diazacrown ethers in the presence of alkali metal carbonates under high-dilution conditions in various organic solvents and their mixtures with water. In the reactions giving rise to diazacrown ethers, alkali metal cations exhibit the negative template effect resulting in a decrease in the yield of the target product if the size of the cation matches well the size of the cavity of the crown ether formed. An N,N"-bis(carboxymethyl) derivative was prepared from the formyl derivative of benzodiaza-18-crown-6.

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Authors and Affiliations

  1. Photochemistry Center, Russian Academy of Sciences, 7a ul. Novatorov, 119421, Moscow, Russian Federation

    O. A. Fedorova, A. I. Vedernikov, I. E. Baronova, O. V. Eshcheulova, E. A. Fedorchuk & S. P. Gromov

  2. Institute of Inorganic Chemistry, D-01062, Dresden, Germany

    K. Gloe

Authors
  1. O. A. Fedorova
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  2. A. I. Vedernikov
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  3. I. E. Baronova
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  4. O. V. Eshcheulova
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  5. E. A. Fedorchuk
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  6. K. Gloe
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  7. S. P. Gromov
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Fedorova, O.A., Vedernikov, A.I., Baronova, I.E. et al. Synthesis of formyl derivatives of benzodiazacrown ethers and benzocryptands. Russian Chemical Bulletin 53, 396–403 (2004). https://doi.org/10.1023/B:RUCB.0000030817.96564.71

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  • DOI: https://doi.org/10.1023/B:RUCB.0000030817.96564.71

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