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■ Cycloaddition of 1-Methoxy-3-trimethylsilyloxybutadiene with Halogenated Carbonyl Compounds

Akira Sera,* Yasuji Iwasaki, Michio Umeda, and Kuniaki Itoh

*Department of Chemistry, Faculty of Science, Kobe University, Nada-Ku, Kobe 6557-8501, Japan

Abstract

Cycloadditions of 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (1) with halogenated carbonyl compounds (2) yielded corresponding substituted tetrahydro- and/or dihydropyran-4-ones (3 and/or 4). Lewis acids were found to be effective as catalysts. Reactions with less reactive carbonyl compounds (2c,d) afforded p-hydroxyacetophenone (5) produced by cyclodimerization of 1. Stereochemistry of the adducts was deduced by ¹H nmr spectroscopy.