Bulletin of the Korean Chemical Society

  • 제16권4호
  • /
  • Pages.363-369
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  • 1995
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Hydroiminoacylation of Allyl and Homoallyl Alcohol Derivatives with Benzalimide and Solvolysis of Hydroacylated Products

  • 발행 : 1995.04.20
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초록

Hydroiminoacylations of allyl and homoallyl alcohol and their derivatives with benzaldimine by Wilkinson's complex have been studied. All these terminal alkene derivatives except allyl alcohol were hydroacylated according to anti-Markownikoff's rule to give the corresponding linear alkyl compounds without showing oxygen directing effect, even though hydroiminoacylation of 3-acetoxy-1,5-hexadiene showed strong allyloxy directing effect over homoallyloxy directing effect in a 92:8 ratio. Solvolysis of 4-acetoxy-1-phenylbutan-1-one, previously prepared by hydroiminoacylation, in ethanol led to etherification giving 4-ethoxy-1-phenylbutan-1-one through neighbouring group participation, while that of 5-acetoxy-1-phenylpentan-1-one led to common transesterification giving 5-hydroxy-1-phenylpentan-1-one. Application of branched alkanols such as isopropanol and t-butanolin solvolysis of 4-acetoxy-1-phenylbutan-1-one underwent competition between etherification and transesterification.

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