Synthesis and Heck Reactions of Ethenyl??and (Z)??Butadien??1??yl Nonaflate Obtained by the Fragmentation of Furan Derivatives

IM Lyapkalo, M Webel…

Index: Lyapkalo, Ilya M.; Webel, Matthias; Reissig, Hans-Ulrich European Journal of Organic Chemistry, 2001 , # 22 p. 4189 - 4194

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Citation Number: 18

Abstract

Abstract The nonaflation of lithium enolates or of silyl enol ethers, formally derived from acetaldehyde or crotonaldehyde, with nonafluorobutanesulfonyl fluoride gave ethenyl nonaflate (1b) and (Z)-buta-1, 3-dien-1-yl nonaflate (2) in good yields. The required enolates were obtained by aldehyde-free routes by the lithiation of tetrahydrofuran or 2, 5- dihydrofuran followed by the cyclofragmentation of the metallated heterocycles. The ...