Tetrahedron

… of nucleophilic centres and the activation of alternative locations to electrophilic attack.: Part III11Part II: AR Katritzky and K. Akutagawa, Tetrahedron, submitted.. A new …

AR Katritzky, WQ Fan, K Akutagawa

Index: Katritzky, Alan R.; Fan, Wei-Qiang; Akutagawa, Kunihiko Tetrahedron, 1986 ,  vol. 42,  # 14  p. 4027 - 4034

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Citation Number: 26

Abstract

N-Methyl-and M-ethyl-aniline are regiospecifically converted into a range of ortho- substituted derivatives, using carbon dioxide both for M-protection and as an intermediate carbanion stabilizing group, and t-butyllithium to lithiate the ortho-carbon atom. The resulting lithium N-(ortho-substituted-phenyl)-N-methyl-and-N-ethyl-carbamates undergo smooth acid- catalysed decarboxylation under mild conditions. No alpha-substituted products were ...