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Synthesis 2006(7): 1111-1116
DOI: 10.1055/s-2006-926383
DOI: 10.1055/s-2006-926383
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of γ-(2,4-Dioxobut-1-ylidene)butenolides by Reaction of Masked 1,3-Dicarbonyl Dianions with Maleic Anhydrides and Phthaloyl Dichloride
Further Information
Received
5 September 2005
Publication Date:
08 March 2006 (online)
Publication History
Publication Date:
08 March 2006 (online)
Abstract
γ-(2,4-Dioxobut-1-ylidene)butenolides were prepared with very good regioselectivity by reaction of (2,4-dioxobutylidene)triphenylphosphoranes with maleic anhydrides. The reaction of 1,3-bis-silyl enol ethers with phthaloyl dichloride afforded benzo-annulated γ-(2,4-dioxobut-1-ylidene)butenolides; the formation of these products can be explained by formation of iso-phthaloyl dichloride and attack of the bis-silyl enol ether onto the latter.
Keywords
butenolides - phosphoranes - O-heterocycles - phthalic acid - silyl enol ethers
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