Formation of phosphoranes from methyl maleanilates and related substrates with triphenylphosphine and their Wittig olefinations with aromatic aldehydes
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An efficient method to obtain phospharanes from triphenylphosphine (TPP) and maleic anhydride (MA), dialkyl maleates, N-aryl maleimides and methyl N-aryl maleanilates is reported. These stabilised phosphoranes react with aromatic aldehydes to yieldE-olefins but fail to react with monoketones and 1,2-diketones. With the more reactive triketone, ninhydrin, the reaction is positive. The order of reactivity of these reagents in olefination appears to be imides=isomaleimides>maleanilates>dialkyl maleates>anhydrides.
KeywordsWittig reactions maleic acid derivatives stabilised phosphoranes
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