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Synthesis of E-1-(alkoxy-NNO-azoxy)-2-arylethenes by the reaction of bis(alkoxy-NNO-azoxy)methanes with benzyl halides under conditions of phase-transfer catalysis

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Abstract

Reaction of bis(methoxy- and ethoxy-NNO-azoxy)methane with benzyl halides and alkali under the conditions of a phase-transfer catalysis furnishes in one stage E-1-(alkoxy-NNO-azoxy)-2-arylethene in 21–55% yields. The intermediate products, 1,1-bis(alkoxy-NNO-azoxy)-2-arylethanes under the action of alkali eliminate one of the two alkoxy-NNO-azoxy groups with the formation of a double bond. The optimum solvent is DMSO, and as benzyl halides, benzyl chlorides. In the case of 4-bromobenzyl bromide a formation was found of a side bisbenzylation product, 1,3-bis(4-bromophenyl)-2,2-bis(methoxy-NNO-azoxy)propane.

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow oblast, 142432, Russia

    I. N. Zyuzin

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  1. I. N. Zyuzin
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Correspondence to I. N. Zyuzin.

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Original English Text © I.N. Zyuzin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 5, pp. 697–703.

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Zyuzin, I.N. Synthesis of E-1-(alkoxy-NNO-azoxy)-2-arylethenes by the reaction of bis(alkoxy-NNO-azoxy)methanes with benzyl halides under conditions of phase-transfer catalysis. Russ J Org Chem 49, 678–685 (2013). https://doi.org/10.1134/S1070428013050072

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  • DOI: https://doi.org/10.1134/S1070428013050072

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