Tetrahedron

Synthesis of meta-substituted aniline derivatives by nucleophilic substitution

AJ Belfield, GR Brown, AJ Foubister, PD Ratcliffe

文献索引：Belfield, Andrew J.; Brown, George R.; Foubister, Alan J.; Ratcliffe, Paul D. Tetrahedron, 1999 , vol. 55, # 46 p. 13285 - 13300

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被引用次数: 33

摘要

Substitution by amines of fluorobenzenes containing a meta-substituted electron withdrawing group (EWG), in DMSO at 100° C over 60 h gave meta-substituted aniline derivatives in isolated yields of up to 98%. The scope of the reaction is explored in terms of reaction conditions and substrates. It is postulated that facile meta-substitutions are facilitated through field stabilisation of the intermediate anion by EWG substituents.