Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Organic Fluorine Compounds. XL. Ring-Opening Reactions of gem-Difluorocyclopropyl Carbinols
小林 義郎森川 勉田口 武夫
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ジャーナル フリー

1983 年 31 巻 8 号 p. 2616-2622

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Three types of ring-opening reactions of gem-difluorocyclopropyl carbinols are described ; 1) reaction with hydrobromic acid, 2) reaction with acetic acid in the presence of p-toluenesulfonic acid, and 3) rearrangement through a mesylate. Ring-opening reactions of 1a, d, e having an electron-donating substituent at C3 were found to give β, β-difluorohomoallyl derivatives derived from C1-C3 bond scission. On the other hand, reactions of 1b, c having hydrogen atoms or a methyl group at C3 were not selective or afforded α, α-difluorohomoallyl derivatives (C1-C2 bond scission) preferentially.
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© The Pharmaceutical Society of Japan
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