The Reduction of <I>gem</I>-Dibromocyclopropanes by Means of Chromium(II) Acetate or Potassium Pentacyanocobaltate

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概要

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• The reduction of <I>gem</I>-dibromocyclopropane(I) with Cr<SUP>II</SUP> acetate in DMSO gives monobromocyclopropanes (II and III) exclusively, whereas the same components in aq DMF afford cyclopropyl acetates(IV and V) as the major products in addition to II and III. A similar substitution on cyclopropane carbon is observed in the reduction of I with K<SUB>3</SUB>Co(CN)<SUB>5</SUB> in DMSO, furnishing cyclopropyl cyanides (IX and X) mainly. The stereochemistry of II, III, IV, and V is determined by the NMR coupling constants and chemical shifts, and that of IX and X, by transformation to the corresponding cyclopropyl methyl ketones derived from cyclopropanecarboxylic acids of known configurations. The reaction of II or III with K<SUB>3</SUB>Co(CN)<SUB>5</SUB> is also described.

• 公益社団法人 日本化学会の論文

著者

• Oshima Koichiro

  Department Of Industrial Chemistry Faculty Of Engineering Kyoto University

• Yamamoto Yasusi

  Department Of Biology Faculty Of Science Kyushu University

• Nozaki Hitosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Yamamoto Yasusi

  Department of Industrial Chemistry, Kyoto University

• Shirafuji Tamio

  Department of Industrial Chemistry, Kyoto University

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