Tetrahedron

Cycloaddition Reactions of Ketene Diethyl Acetal toward the Synthesis of Cyclobutene Monomers

CS Kniep, AB Padias, HK Hall

Index: Kniep, Carina S.; Padias, Anne B.; Hall Jr. Tetrahedron, 2000 , vol. 56, # 25 p. 4279 - 4288

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Citation Number: 16

Abstract

The [2+ 2]-cycloaddition reactions of ketene diethyl acetal with methyl acrylate and acrylonitrile were optimized. Highly efficient ketal cleavage to either 2-cyano-1- cyclobutanone or 2-methoxycarbonyl-1-cyclobutanone was achieved using formic acid. Among the numerous reduction methods attempted, only sodium cyanoborohydride in acidic medium led successfully to the corresponding alcohols, but isolation of the desired ...

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