Carbon-Carbon Bond Formation by Use of Chloroiodomethane as a C1 Unit. I. Formation of Chloromethyltriphenylphosphonium Iodide, and Its Application for the Wittig Chloromethylenation of Aldehydes and Ketones

DOI DOI PDF 被引用文献3件 参考文献13件 オープンアクセス
  • Sotaro Miyano
    Department of Applied Chemistry, Faculty of Engineering, Tohoku University
  • Yu Izumi
    Department of Applied Chemistry, Faculty of Engineering, Tohoku University
  • Katsuo Fujii
    Department of Applied Chemistry, Faculty of Engineering, Tohoku University
  • Yutaka Ohno
    Department of Applied Chemistry, Faculty of Engineering, Tohoku University
  • Harukichi Hashimoto
    Department of Applied Chemistry, Faculty of Engineering, Tohoku University

書誌事項

公開日
1979-04-01
権利情報
  • https://academic.oup.com/pages/standard-publication-reuse-rights
DOI
  • 10.1246/bcsj.52.1197
  • 10.1002/chin.197930175
公開者
Oxford University Press (OUP)

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<jats:title>Abstract</jats:title> <jats:p>Chloromethyltriphenylphosphonium iodide has been prepared by the reaction of chloroiodomethane with triphenylphosphine. Upon treatment with potassium t-butoxide in t-butyl alcohol, the phosphonium iodide was converted into chloromethylenetriphenylphosphorane; this in turn was used for the Wittig reaction of aldehydes and ketones into the corresponding chloroolefins of the type RCH=CHCl and RR′C=CHCl in good to moderate yields. The configurations of these chloroolefins were assigned on the basis of NMR spectral studies. Direct conversion of benzaldehyde into phenylacetylene was also achieved using the phosphonium salt and excess potassium t-butoxide.</jats:p>

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