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Polybromoaromatic Compounds: IX. Reactions of Polybromobenzyl Bromides with Enolates Derived from Some Dicarbonyl Compounds

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Abstract

The reaction of polybromobenzyl bromides RC6Br4CH2Br (R = Br, OCH3) with diethyl malonate sodium salt in ethanol and dimethylformamide leads to formation of diethyl 2-(polybromobenzyl)malonates, whereas in aqueous ethanol ethyl polybromobenzyl malonates are formed. The same polybromobenzyl bromides react with an equimolar amount of ethyl acetoacetate sodium salt or acetylacetone sodium salt to give C-alkylation products; with excess sodium enolates ethyl 3-(polybromophenyl)propionates and 4-(polybromophenyl)-2-butanones are formed, respectively.

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Authors and Affiliations

  1. Ogarev Mordovian State University, ul. Bol'shevistskaya 68, Saransk, 430000, Russia

    V. N. Shishkin, S. S. Vakaeva, A. I. Belozerov & B. S. Tanaseichuk

  2. Faculty of Chemistry, Moscow State University, Vorob'evy gory, Moscow, 119899, Russia

    K. P. Butin

Authors
  1. V. N. Shishkin
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  2. S. S. Vakaeva
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  3. A. I. Belozerov
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  4. B. S. Tanaseichuk
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  5. K. P. Butin
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Shishkin, V.N., Vakaeva, S.S., Belozerov, A.I. et al. Polybromoaromatic Compounds: IX. Reactions of Polybromobenzyl Bromides with Enolates Derived from Some Dicarbonyl Compounds. Russian Journal of Organic Chemistry 37, 975–980 (2001). https://doi.org/10.1023/A:1012474416163

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  • DOI: https://doi.org/10.1023/A:1012474416163

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