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Paper | Regular issue | Vol 36, No. 9, 1993, pp.2139-2145
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6434
Thermal Cycloaddition of Aroylketene to 1-Aryl-1-trimethylsilyloxyethylene: A Simple Synthesis of 2,6-Diaryl-4H-pyran-4-one

Takehiro Sano,* Toshiaki Saitoh, and Jun Toda

*Showa college of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

Abstract

Aroylketene (2) generated by pyrolytic decarbonylation of 5-aryl-2,3-dihydro-2,3-furandione (1) reacted with 1-aryl-1-trimethylsilyloxyethylene (3) in a regioselective manner to give 2,6-diaryl-4H-pyran-4-one (5) and/or 1,5-diarylpentane-1,3,5-trione (6). This reaction provides a simple synthetic method of 2,6-diaryl-4H-pyran-4-one with various substituents in the aryl goup.