Synthesis of 1, 4-Diketones from Acylcarbonylferrates and Methyl Vinyl Ketone

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Other Title
  • アシルカルボニル鉄酸塩とメチルビニルケトンの反応による1,4-ジケトンの合成
  • アシルカルボニル テツ サンエン ト メチルビニルケトン ノ ハンノウ ニ ヨ
  • Application to the Synthesis of <I>cis</I>-Jasmone and Dihydrojasmone
  • <I>cis</I>-ジャスモンとジヒドロジャスモン合成への応用

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Abstract

The reactions of acylcarbonylferrates with methyl vinyl ketone were investigated and found to result in the formation of 1, 4-diketones in good yields under mild reaction conditions, <BR>R-Br K2Fe(CO)4→K+[RCOFe(CO)3L]- CH2=CHCOCH3 →R-COCH2CH2COCH3<BR>The reactions were variously affected accodrding to the solvents used. Dipolar aprotic solvents such as N, N-dimethylacetamide promoted the reactions but in tetrahydrofuran, they did not proceed.<BR>Using the present method, important perfume substances such as cis-jasmone and dihydrojasmone could be prepared in good over-all yield in one pot.

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