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Chemistry of 1, 3-Cyclohexanedione

Communication 5. Chemical properties of enolethers of 1,3-cyclohexanedione and its derivatives

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Reaction of 6-methoxy-2-naphthylmagnesium bromide with the enol ether, 3-methoxy-2-methyl-2-cyclohexen-1-one (VIII), and subsequent hydrolysis with hydrochloric acid gave the tricyclic ketone (XI).

  2. 2.

    Bromination of 3-methoxy-2-cyclohexen-1-one (I) and 3-methoxy-2-methyl-2 cyclohexen-1-one (VIII) and subsequent treatment of the intermediate dibromides (II) and (IX) with aqueous sodium carbonate gave 2-bromo-3-methoxy-2-cyclohexen-1-one (III) and probably 6-bromo-3-methoxy-2-methyl-2-cyclohexen-1-one (X), respectively. 3. 3-Methoxy-2-cyclohexen-1-one (I) and 3-methoxy-2-methyl-2-cyclohexen-1-one (VIII) are reduced by lithium in liquid ammonia with formation of cyclohexanone and 2-methylcyclohexanone, respectively.

  3. 4.

    3-Methoxy-2-cyclohexen-1-one (I) undergoes the Claisen reaction with formic and oxalic esters at the methylene group in the 6-position.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    S. I. Zav'yalov & G. V. Kondrat'eva

Authors
  1. S. I. Zav'yalov
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  2. G. V. Kondrat'eva
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Zav'yalov, S.I., Kondrat'eva, G.V. Chemistry of 1, 3-Cyclohexanedione. Russ Chem Bull 9, 1328–1332 (1960). https://doi.org/10.1007/BF00907664

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  • DOI: https://doi.org/10.1007/BF00907664

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