The reaction of 2-chloroazulene derivatives with lithium acetylide in liquid ammonia.

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  • Morita Tadayoshi
    Department of Chemistry, Faculty of Science, Tohoku University
  • Fujita Taira
    Department of Chemistry, Faculty of Science, Tohoku University
  • Takase Kahei
    Department of Chemistry, Faculty of Science, Tohoku University

Description

The reaction of diethyl 2-chloroazulene-1,3-dicarboxylate (1a) with lithium acetylide in liq ammonia gave diethyl 4- and 6-ethynylazulene-1,3-dicarboxylates by an abnormal substitution reaction. In a similar manner, some 2-chloroazulenes, possessing alkoxycarbonyl and/or cyano substituents at the 1- and 3-positions of azulene nucleus, gave the corresponding 4 (or 8)- and 6-ethynylazulenes. The same type reaction proceeded when lithium phenylacetylide, sodium indenide, and sodium fluorenide were used as the reagents, 1a giving diethyl 4- and 6-(phenylethynyl)-, 6-(3-indenyl)-, and 6-(9-fluorenyl)azulene-1,3-dicarboxylates, respectively.

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