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Synthesis 1971; 1971(8): 415-422
DOI: 10.1055/s-1971-21750
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Halogenated Ketenes: Valuable Intermediates in Organic Synthesis1

William T. BRADY*
  • *Department of Chemistry, North Texas State University, Denton, Texas 76201, U.S.A.
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Publication Date:
12 September 2002 (online)

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The preparation and 1,2-cycloaddition of halogenated ketenes with olefins and other unsaturated compounds is described. Many illustrations of the formation of α-halo- and α,α-dihalocyclobutanones and other 4-membered rings are given. The usefulness of halogenated ketenes in synthesis is demonstrated by some examples of the conversion of dihalo- and alkylhaloketene cycloadducts with cyclopentadiene to tropone derivatives. Further utility is shown by some ring contraction reactions of the cyclobutanones and cyclobutanols to cyclopropane derivatives.

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