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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 7, Number 3
March 20, 1986 

Synthesis of (E,E)-2,4-Dienols from (E)-β-Chloro-γ-hydroxy-vinylmercurials and Olefins by Palladium(Ⅱ) Salt
Jin Il Kim*, Jong Tae Lee, Cheol Kyu Choi
Reaction of (E)-β-chloro-γ -hydroxyvinylmercurials, prepared by mercuration of propargyl alcohol and 2-methyl-3-butyne-2-ol, with olefins in the presence of a catalytic amount of Li2PdCl4 and 2 equiv of cupric chloride in methanol at 50℃ gave the corresponding (E,E)-2,4-dienols in moderate yields. However, addition of 1 equiv of inorganic bases such as magnesium oxide to the reaction mixture brings a rapid and clean vinylation and gave high yields of the dienols at room temperature. In the case of hindered (E)-2-chloro-3-chloromercuri-2-buten-1,4-diol prepared from 2-butyne-1,4-diol, reaction with olefins gave the dienols only in low yields even in the presence of 2 equiv of magnesium oxide.
235 - 237
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