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1-Phenylselanylazulenes: synthesis and selenium atom oxidation

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Abstract

The phenylselanylation of azulene with PhSeCl or PhSeBr was reported. Clean electrophilic substitution of azulene in positions 1 and/or 3 occurred with the first reagent whereas with PhSeBr a complex mixture of products was generated suggesting a radicalic mechanism. The influence on the reaction route of the substituent attached at position 1 of azulene, or of the alkyl positions in alkylated azulenes was investigated. 1-Phenylselanylazulene and 1,3-bis(phenylselanyl)azulene were oxidized using sodium metaperiodate. The oxidation took place at selenium atom and afforded azulenes substituted with PhSe(O) and/or PhSe(O2) groups in positions 1 and/or 3. The magnetic and electronic spectra as well as the electrochemical oxidation and reduction potentials of the obtained products were recorded and the results were briefly discussed.

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Authors and Affiliations

  1. Romanian Academy, Institute of Organic Chemistry “C. D. Nenitzescu”, Spl. Independentei, 202B, P.O. Box 15-254, 060023, Bucharest, Romania

    Alexandru C. Razus, Liviu Birzan, Anamaria Hanganu & Mihaela Cristea

  2. Faculty of Applied Chemistry and Material Sciences, University “Politehnica” of Bucharest, Gh. Polizu 1-7, 011061, Bucharest, Romania

    Eleonora-Mihaela Ungureanu, Maria-Laura Soare & George-Octavian Buica

Authors
  1. Alexandru C. Razus
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  2. Liviu Birzan
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  3. Anamaria Hanganu
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  4. Mihaela Cristea
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  5. Eleonora-Mihaela Ungureanu
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  6. Maria-Laura Soare
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  7. George-Octavian Buica
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Corresponding authors

Correspondence to Liviu Birzan or Eleonora-Mihaela Ungureanu.

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Razus, A.C., Birzan, L., Hanganu, A. et al. 1-Phenylselanylazulenes: synthesis and selenium atom oxidation. Monatsh Chem 145, 1999–2009 (2014). https://doi.org/10.1007/s00706-014-1297-3

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  • DOI: https://doi.org/10.1007/s00706-014-1297-3

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