Carbon-carbon bond formation by the use of chloroiodomethane as a C1 unit. II. The preparation and synthetic application of 1-chloro-3-iodoheptane.

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概要

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• Terminal alkenes, R–CH=CH<SUB>2</SUB> (R=Et, <I>n</I>-Pr, <I>n</I>-Bu, <I>n</I>-Hex), were readily transformed into 1-chloro-3-iodoalkanes by the AIBN-induced free radical addition of chloroiodomethane. Thus, 1-chloro-3-iodoheptane was obtained from 1-hexene in an 88% yield; this in turn was allowed to react with dialkyl malonates in the presence of alkoxides in alcohols to give dialkyl 2-butylcyclobutane-1,1-dicarboxylates and dialkyl (<I>E</I>)-3-octene-1,1-dicarboxylates (<B>7</B>), either of which could be obtained preferentially by the choice of the experimental parameters. The olefinic product, <B>7</B>, was further utilized for the synthesis of (<I>E</I>)-5-decenyl acetate and/or 1,4-nonanolide.

• 公益社団法人 日本化学会の論文

著者

• Hashimoto Harukichi

  Department of Applied Chemistry, Faculty of Engineering, Tohoko University

• Miyano Sotaro

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

• Hokari Hiroshi

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

• Umeda Yoshiharu

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

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