Tetrahedron

X= Y-ZH Systems as Potential 1, 3-Dipoles. Part 45. 1, 2 Proton Sponge Effects on the 1, 2-Prototropic Formation of Azomethine Ylides from Arylidene Benzylamines

R Grigg, P McMeekin, V Sridharan

Index: Grigg, Ronald; McMeekin, Peter; Sridharan, Visuvanathar Tetrahedron, 1995 , vol. 51, # 48 p. 13331 - 13346

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Citation Number: 10

Abstract

A strong rate enhancing effect of an ortho-methoxy or an ortho-dimethylamino group on the 1, 2-prototropic generation of azomethine ylides from arylidene arylmethylamines is demonstrated. In the absence of such functionality azomethine ylide formation fails to occur in boiling xylene. The reactions generate the E, E-or syn-azomethine ylide stereoselectively if a single ortho-OMe or-NMe2 group is present or stereospecifically if either bifurcated H- ...