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Synthesis, characterization of N-, S-, O-substituted naphtho- and benzoquinones and a structural study

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Abstract

The new series of N-, S-, O-substituted 1,4-naphthoquinone and S-, O-substituted 1,4-benzoquinone compounds were synthesized via vinylic substitution. Compounds 3 and 4 were synthesized from the reaction of 1 with 2. Compounds 6, 7 and 8 were synthesized from reaction of 1 with 5. Compounds 10 and 11 were obtained from the reaction of 1 with 9. Compounds 13 and 14 were synthesized from the reaction of 1 with 12. Compounds 16 and 17 were obtained from the reaction of 15 with 2. Photochemical and electrochemical properties of N-, S-, O-substituted quninone compounds were determined by using fluorescence spectroscopy and cyclic voltammetry. Crystal structure of 2-(7-sulphanyl-4-methyl-coumarinyl)-3-(1-ethoxy)-1,4-naphthoquinone 13 was determined by X-ray diffraction method.

The new series of heteroatom substituted 1,4-naphtho- and 1,4-benzoquinone compounds were synthesized via vinylic substitution. Photo- and electrochemical properties of N-, S-, O-substituted quinone compounds were investigated by fluorescence spectroscopy and cyclic voltammetry. The structure of 2-(7-sulfanyl-4-methyl-coumarinyl)-3-(1-ethoxy)-1,4-naphthoquinone 13 was determined by X-ray diffraction method.

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Authors and Affiliations

  1. Engineering Faculty, Department of Chemistry, Division of Organic Chemistry, Istanbul University, 34320, Avcilar Istanbul, Turkey

    CEMIL IBIS & NAHIDE GULSAH DENIZ

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  1. CEMIL IBIS
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  2. NAHIDE GULSAH DENIZ
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Correspondence to CEMIL IBIS.

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IBIS, C., DENIZ, N.G. Synthesis, characterization of N-, S-, O-substituted naphtho- and benzoquinones and a structural study. J Chem Sci 124, 657–667 (2012). https://doi.org/10.1007/s12039-012-0252-2

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  • DOI: https://doi.org/10.1007/s12039-012-0252-2

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