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An Efficient Method for Generation of α-Oxoketenes: Cycloreversion of Enolized Meldrum's Acid Derivatives

M Sato, H Ban, C Kaneko

Index: Sato, Masayuki; Ban, Hitoshi; Kaneko, Chikara Tetrahedron Letters, 1997 , vol. 38, # 38 p. 6689 - 6692

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Citation Number: 41

Abstract

A series of 6-methoxy-or siloxy-4H-1, 3-dioxin-4-ones was synthesized from Meldrum's acids. These dioxinones underwent 4+ 2 cycloreversion to methoxy-or siloxycarbonylketenes and ketones quantitatively at 20–50° C. The ketenes were characterized by IR spectroscopy as well as by trapping with t-butanol. The ready cycloreversion of these enolized Meldrum's acid derivatives strongly indicates that the ...