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Synthesis of gem-Dichlorocyclopropane Derivatives Containing 1,3-Dioxolane Fragments

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Abstract

The reaction of 2-phenyl-gemdichlorocyclopropane or (2,2-dichlorocyclopropyl)benzene with ethyl alcohol in the presence of solid alkali gave phenylacrolein diethyl acetal or (2,2-diethoxy-1-methylethyl)benzene, which, upon subsequent dichlorocarbenation and transacetalization with ethylene glycol, formed 2-(2,2-dichloro-1-phenylcyclopropyl)-1,3-dioxolane. Thus, two approaches to the synthesis of a product simultaneously containing gem-dichlorocyclopropane and 1,3-dioxolane fragments have been proposed. It has been established that the best method is sequential dichlorocarbenation of [1-(di-ethoxymethyl)ethenyl]benzene and acetalization of the resulting product to form the target molecule: 2-(2,2-dichloro-1-phenylcyclopropyl)-1,3-dioxolane. The structure of the reaction products was confirmed by 1H and 13C NMR spectroscopy and chromato-mass spectrometry.

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Authors and Affiliations

  1. Ufa State Petroleum Technological University, 450062, Ufa, Russia

    G. N. Sakhabutdinova, G. Z. Raskil’dina, R. R. Chanyshev & S. S. Zlotskii

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  1. G. N. Sakhabutdinova
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  2. G. Z. Raskil’dina
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  3. R. R. Chanyshev
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  4. S. S. Zlotskii
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Correspondence to G. N. Sakhabutdinova.

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Translated by S. Avodkova

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Sakhabutdinova, G.N., Raskil’dina, G.Z., Chanyshev, R.R. et al. Synthesis of gem-Dichlorocyclopropane Derivatives Containing 1,3-Dioxolane Fragments. rev. and adv. in chem. 12, 255–258 (2022). https://doi.org/10.1134/S263482762370006X

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