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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 16, Number 4
BKCSDE 16(4)
April 20, 1995

Title	Hydroiminoacylation of Allyl and Homoallyl Alcohol Derivatives with Benzaldimine and Solvolysis of Hydroacylated Products
Author	Jun-Bae Hong, Chul-Ho Jun*
Keywords
Abstract	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.
Page	363 - 369
Full Text	PDF

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