Tetrahedron

An unusual behaviour of N-(tert-butoxycarbonyl)-and N-pivaloyl-(methylthio) anilines in metallation reactions

MG Cabiddu, S Cabiddu, E Cadoni, S De Montis…

文献索引：Cabiddu, Maria Grazia; Cabiddu, Salvatore; Cadoni, Enzo; De Montis, Stefania; Fattuoni, Claudia; Melis, Stefana Tetrahedron, 2003 , vol. 59, # 16 p. 2893 - 2897

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被引用次数: 5

摘要

The metallation reaction of N-Boc-and N-Piv-(methylthio) anilines are here described. The results show that N-Boc derivatives are metallated only by superbases to give products substituted at the thiomethylic group. N-Piv derivatives show a different behaviour: ortho- derivative is metallated by both butyllithium and superbase at the thiomethylic carbon atom, while para-derivative is metallated in ortho to the N-Piv group by butyllithium and at the ...