Reduction of acetals with TiCl4-LiAlH4.

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概要

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• The reduction of dialkyl acetals derived from aromatic aldehydes and ketones with TiCl<SUB>4</SUB>–LiAlH<SUB>4</SUB> in THF or diethyl ether at room temperature afforded the coupling products, pinacol ethers or olefins, in high yields. On the other hand, when acetals derived from aliphatic aldehydes and ketones were treated with TiCl<SUB>4</SUB>–LiAlH<SUB>4</SUB> in diethyl ether, the reductive dealkoxylation took place and the corresponding ethers were isolated in good yields. As to the reaction mechanism we propose that Ti(II) is the reactive species in reductive coupling reaction of acetals derived from aromatic aldehydes and ketones, and that Ti(0)–H<SUB>2</SUB>AlCl complex may be the reactive species in reductive dealkoxylation of acetals derived frcm aliphatic aldehydes and ketones.

• 公益社団法人 日本化学会の論文

著者

• Mukaiyama Teruaki

  Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo

• Ishikawa Hiroshi

  Laboratories of Medicinal Chemistry, Otsuka Pharmaceutical Co., Ltd.

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