Syntheses of Isoprenoids by Telomerizations. IX. Stereoselectivity of Telomers and the Effect of Telogens in Anionic Telomerizations Using Secondary Amines

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概要

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• The stereoselectivity of the telomers and the effect of the telogens in the anionic telomerizations of isoprene with secondary amines were investigated. Dimethyl-, diethyl-, di-<I>n</I>-propy-1, diisopropyl-, and methylphenyl-amines, pyrrolidine, morpholine, and piperidine were used as the telogens. The ratio of <I>N</I>,<I>N</I>-dialkyl(3,7-dimethyl-2,6-octadienyl)amine(<B>2A</B>) to <I>N</I>,<I>N</I>-dialkyl(2-isopropenyl-5-methyl-4-hexenyl)amine(<B>2B</B>), which were obtained in these reactions, was varied with the sort of secondary amines, the yield of the telomers was found to be dependent on the acidity of the secondary amines. Moreover, <B>2A</B>, which was the main component of the <I>n</I>=2 telomers, was confirmed to have a <I>cis</I>-configuration—that is, <I>N</I>,<I>N</I>-dialkylnerylamine. However, the <I>n</I>=1 telomer of myrcene with secondary amine was <I>N</I>,<I>N</I>-dialkylgeranylamine. These results were interpreted in terms of the stability of the cyclic intermediate of the carbanions.

• 公益社団法人 日本化学会の論文

著者

• Tanaka Juntaro

  Department Of Laboratory Medicine Okayama University Medical School

• Takabe Kunihiko

  Department Of Applied Chemistry Faculty Of Engineering Shizuoka University

• Katagiri Takao

  Department of Synthetic Chemistry, Faculty of Engineeing, Shizuoka University

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