Intramolecular conversions of acyllithium. Cyclization in the reaction of carbon monoxide with [1-(silyl) vinyl] lithium

…, Y Hayama, A Hirai, N Sonoda, A Orita…

Index: Ryu, Ilhyong; Hayama, Yoshihiko; Hirai, Akira; Sonoda, Noboru; Orita, Akihiro; Ohe, Kouichi; Murai, Shinji Journal of the American Chemical Society, 1990 , vol. 112, # 19 p. 7061 - 7063

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Citation Number: 35

Abstract

We have discovered that the lithium enolate of 2-(trimethylsi1yl) cyclopropanone is formed by the reaction of [1-(trimethylsilyl) vinyl] lithium (la) 5 with CO. Treatment of la with an atmospheric pressure of CO in THF at 15 OC for 2 h followed by quenching with chlorotrimethylsilane at-78 OC afforded a somewhat labile product, which decomposed during the ordinary hydrolytic workup. Quenching with tert-butyldimethylchloro-silane/ ...