Synthesis of New Cyclic Ketones from Various Conjugated Diene Hydrocarbons

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  • FUJITA Tsutomu
    Department of Applied Chemistry, Faculty of Engineering, Chiba University
  • WATANABE Shoji
    Department of Applied Chemistry, Faculty of Engineering, Chiba University
  • SUGA Kyoichi
    Department of Applied Chemistry, Faculty of Engineering, Chiba University
  • YOKOYAMA Toshiro
    Department of Applied Chemistry, Faculty of Engineering, Chiba University

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  • 共役ジエン炭化水素を原料とする新しい環状ケトン類の合成
  • キョウヤク ジエン タンカ スイソ オ ゲンリョウ ト スル アタラシイ カン

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Two types of new cyclic ketones were prepared from conjugated hydrocarbons by the combination of Diels-Alder reaction, Grignard reaction and cyclization.<BR>(1) New cyclohexenyl alkenyl ketones were obtained by the reaction of various methyl cyclohexenyl carboxylates and vinylmagnesium chloride; for example, 1- (4'-methyl-3'-cyclohexen-1'-yl) -4-penten-1-one was produced from methyl 4-methyl-3-cyclohexen-1-carboxylate and vinylmagnesium chloride.<BR>(2) Several hydroindene derivatives were prepared from 2, 7-dimethyl-1, 3, 7-octatriene via Diels Alder reaction followed by acidic cyclization ; for example, a mixture of 2-acetyl-5, 7, 7-trimethylbicyclo [4, 3, 0] non -1 (6) -ene, 2-acetyl-5, 7, 7-trimethylbicyclo [4, 3, 0] non-1-ene and 2-isopropyl-3, 6-dimethylindene was obtained by the cyclization of 4-acetyl-1-methyl-3- (3'-methyl-3'-butenyl) -1-cyclohexene.

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