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2,2′-Bis[(chloromethyl)diorganylsilyloxy]azobenzenes

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Abstract

Previously unknown 2,2′-bis(silyloxy)azobenzenes containing a carbon functional group on the silicon atom have been synthesized. The reaction of 2,2′-dihydroxyazobenzene with chlorosilanes R1R2(ClCH2)SiCl (R1 = R2 = Me; R1 = OBu-t, R2 = Me) in the presence of triethylamine led to the formation of the corresponding 2,2′-bis[(chloromethyl)diorganylsilyloxy]azobenzenes which underwent intramolecular cyclization on prolonged storage at room temperature to produce more stable cyclic azobenzenes with an N=N→Si transannular dative bond, 6,6-dimethyldibenzo- and 6-(chloromethyl)-6-methyldibenzo[d,h][1,3,6,7,2]dioxadiazasilonines. A probable mechanism of the process is discussed.

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ACKNOWLEDGMENTS

The spectral and analytical data were obtained using the facilities of the Baikal joint center, Siberian Branch, Russian Academy of Sciences.

Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 19-03-00143).

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Authors and Affiliations

  1. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    A. S. Soldatenko & N. F. Lazareva

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  1. A. S. Soldatenko
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  2. N. F. Lazareva
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Correspondence to N. F. Lazareva.

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To the 100th Anniversary of M.G. Voronkov

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Soldatenko, A.S., Lazareva, N.F. 2,2′-Bis[(chloromethyl)diorganylsilyloxy]azobenzenes. Russ J Gen Chem 91, 2416–2423 (2021). https://doi.org/10.1134/S1070363221120094

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  • DOI: https://doi.org/10.1134/S1070363221120094

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