Abstract

Contrary to N-lithium-N-methylanilide and N-lithium-diphenylamide, trimethyl-N-lithium-N-phenyl-silylamide gave with hexafluorobenzene in molar ratio 2:1, only the monosubstituted compound. Competitive reactions gave the following order of reactivity toward N-lithiumanilide: 2,3,4,5,6-pentafluorotriphenylamine > 2,3,4,5,6-pentafluoro-N-methyl-diphenylamine > hexafluorobenzene ⪢ trimethyl-2,3,4,5,6-pentafluoro-N,N-diphenyl-silylamine. A reason for the low reactivity of trimethyl-2,3,4,5,6-pentafluoro-N,N-diphenyl-silylamine against aromatic amides has been proposed. Some new aromatic amines have been synthesized, among them hexamethyl-N-pentafluorophenyl-disilylamine.

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