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Reactions of [(3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dien- 1-ylidene)methyl]phosphonates with Phenols

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Abstract

Dialkyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonates reacted with phenol and benzenediols in the presence of trifluoromethanesulfonic acid to give products of electrophilic substitution in the benzene ring, the corresponding diarylmethylphosphonates or [phenylenebis(arylmethylene)]- diphosphonates. The reaction of diphenyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonate with 2-methylbenzene-1,3-diol at a ratio of 1: 1 afforded 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-6-hydroxy-7-methyl-2-phenoxy-2,3-dihydro-1,2λ5-benzoxaphosphol-6-one.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences,”, ul. Akad. Arbuzova 8, Kazan, Tatarstan, 420088, Russia

    E. M. Gibadullina, T. R. Shaekhov, Yu. K. Voronina, M. A. Pudovik & A. R. Burilov

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  1. E. M. Gibadullina
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  2. T. R. Shaekhov
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  3. Yu. K. Voronina
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  4. M. A. Pudovik
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  5. A. R. Burilov
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Correspondence to E. M. Gibadullina.

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Original Russian Text © E.M. Gibadullina, T.R. Shaekhov, Yu.K. Voronina, M.A. Pudovik, A.R. Burilov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 4, pp. 532–538.

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Gibadullina, E.M., Shaekhov, T.R., Voronina, Y.K. et al. Reactions of [(3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dien- 1-ylidene)methyl]phosphonates with Phenols. Russ J Org Chem 54, 530–536 (2018). https://doi.org/10.1134/S1070428018040036

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  • DOI: https://doi.org/10.1134/S1070428018040036

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