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No.82 (2006/10) >

Title :Reaction of 5$\alpha$-Cholest-2-ene with Iodine-Copper (2) Acetate
Authors :Utsukihara, Takamitsu
Yokoyama, Yuuya
Kaneko, Katsuo
Yoshino, Isao
Miyasaka, Tohru
Satoh, J. Yasuo
Kuniyoshi, Masayuki
Horiuchi, C. Akira
Authors alternative :国吉, 正之
Issue Date :Oct-2006
Abstract :Reaction of 5$\alpha$-cholest-2-ene (1) with iodine (2.0mol equiv) and copper (2) acetate (2.0mol equiv) in acetic acid under refluxing yielded 5$\alpha$-cholestane-2$\beta$, 3$\beta$-diol 2-acetate (4) (13%), 2-iodoacetate (5) (55%), 3-iodoacetate (6) (10%), and 2-iodoacetate 3-acetate (7) (13%). Then the hydrolysis of these reaction mixtures afforded the more hindered 2$\beta$, 3$\beta$-diol (13) in good yield. In the case of cyclohexene (2), the similar compounds were obtained. In order to clarify the reaction pathway of the unexpected hydroxy iodoacetate, the reaction of cis-hydroxy acetate with iodine-copper(2) acetate was carried out. It was found that copper is coordinated to the oxygen of the hydroxyl group and the carbonyl group of the acetate so that the methyl group of the acetate may be activated, and then iodination occurs at the acetoxyl group.
Type Local :紀要論文
ISSN :0286-9640
Publisher :琉球大学理学部
URI :http://hdl.handle.net/20.500.12000/5372
Citation :琉球大学理学部紀要 = Bulletin of the College of Science. University of the Ryukyus no.82 p.77 -87
Appears in Collections:No.82 (2006/10)

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