高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (S1): 497.

• Synthetic Sciences • 上一篇    下一篇

A New Route for the Preparation of α,ω-Diacetylalkanes from Diacids and Enacid

GAO Zhu-Lin, YIN Cai-Xia, LIU Fu-Chu   

  1. Departement of Chemistry, Yunnan University, Kunming 650091
  • 出版日期:2000-12-31 发布日期:2000-12-31
  • 基金资助:

    Supported by Yunnan Applied and Basic Research Foundation (98C017M).

A New Route for the Preparation of α,ω-Diacetylalkanes from Diacids and Enacid

GAO Zhu-Lin, YIN Cai-Xia, LIU Fu-Chu   

  1. Departement of Chemistry, Yunnan University, Kunming 650091
  • Online:2000-12-31 Published:2000-12-31
  • Supported by:

    Supported by Yunnan Applied and Basic Research Foundation (98C017M).

摘要:

Methyl ketones are important intermediates for the synthesis of methyl alkyl carbionols, annulation reagents, and cyclic compounds. There have been some methods to get methyl ketones such as alkylation of actone derivatives, hydration of olefins and acethylenes using mercury compounds. Compared with these methods, the palladium-catalyzed oxidation of α-olefins is more convenient and practical. Use of DMF as a solvent for the oxidation of α-olefins has been reported by Clement and Selwitz[1]. The method requires only a catalytic amount of PdCl2 and gives satisfactory yields, under mild conditions. This usefully sythetic method for preparation of methyl ketones has been applied extensively in syntheses of natural products such as steriods[2] and muscone[3]. Although a considerable number of studies have been carried out on palladium-catalyzed oxidation, they were done mostly with α-olefins. We paid attention to the usefulness of the reaction as a synthetic method for α,ω-diacetylalkanes from α,ω-olefins. The preparation of diolefins from diacids has not been reported in the previous literatures. Herein,we described our route for preparation of α,ω-diacetylalkanes.

Abstract:

Methyl ketones are important intermediates for the synthesis of methyl alkyl carbionols, annulation reagents, and cyclic compounds. There have been some methods to get methyl ketones such as alkylation of actone derivatives, hydration of olefins and acethylenes using mercury compounds. Compared with these methods, the palladium-catalyzed oxidation of α-olefins is more convenient and practical. Use of DMF as a solvent for the oxidation of α-olefins has been reported by Clement and Selwitz[1]. The method requires only a catalytic amount of PdCl2 and gives satisfactory yields, under mild conditions. This usefully sythetic method for preparation of methyl ketones has been applied extensively in syntheses of natural products such as steriods[2] and muscone[3]. Although a considerable number of studies have been carried out on palladium-catalyzed oxidation, they were done mostly with α-olefins. We paid attention to the usefulness of the reaction as a synthetic method for α,ω-diacetylalkanes from α,ω-olefins. The preparation of diolefins from diacids has not been reported in the previous literatures. Herein,we described our route for preparation of α,ω-diacetylalkanes.

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