Condensation of lithium diphenylphosphonium diylides with carbonic anhydride derivatives. A new one-pot synthesis of α, β-unsaturated anilides and amidines.

HJ Cristau, A Perraud-Darcy, Y Ribeill

Index: Cristau, Henri-Jean; Perraud-Darcy, Anne; Ribeill, Yves Tetrahedron Letters, 1992 , vol. 33, # 19 p. 2693 - 2696

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Citation Number: 9

Abstract

Abstract Lithium diphenylphosphonium diylides readily attack phenylisocyanate and dicyclohexylcarbodiimide. The formed semi-stabilised ylides bear a metallated amide or amidine function. Their use in situ as Wittig reagents towards aldehydes and ketones is shown to be a new one-pot, E-stereoselective synthesis for αβ-unsaturated anilides and amidines. Moreover, the corresponding phosphonium salts were isolated.