The Journal of Organic Chemistry

The scope and limitations of carboxamide-induced. beta.-directed metalation of 2-substituted furan, thiophene, and 1-methylpyrrole derivatives. Application of the …

AJ Carpenter, DJ Chadwick

Index: Carpenter, Andrew J.; Chadwick, Derek J. Journal of Organic Chemistry, 1985 , vol. 50, # 22 p. 4362 - 4368

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Citation Number: 44

Abstract

The effects of change of solvent, metalating agent, reaction time, and reaction temperature on the lithiation of N, N-diethylthiophene-2-carboxamide and of the N-tert-butyl2- carboxamide derivatives of furan, thiophene, and 1-methylpyrrole are explored, and optimum conditions are established for ring P-directed metalation. The tertiary carboxamido group is less effective in this context than the secondary amide function and appears to be ...