Journal of Fluorine Chemistry

Regiospecific α-hexafluoroisopropylidenation of ketones using hexafluoroacetone

T Ishihara, H Shinjo, Y Inoue, T Ando

Index: Ishihara, Takashi; Shinjo, Hiroshi; Inoue, Yoshihisa; Ando, Teiichi Journal of Fluorine Chemistry, 1983 , vol. 22, p. 1 - 20

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Citation Number: 20

Abstract

Abstract Hexafluoroacetone (HFA) reacted regiospecifically with various enol silyl ethers at− 30 to− 35 C in the presence of a Lewis acid to give HFA aldols, or α-bis (trifluoromethyl) hydroxymethyl carbonyl compounds, in good yields. The reaction of HFA with dienol silyl ethers, on the other hand, cleanly proceeded even in the absence of a Lewis acid to provide [4+ 2] cycloadducts, or bistrifluoromethylated tetrahydropyran-4-one derivatives, ...