Lithium N-lithiomethyldithiocarbamates: New N-alkylaminomethyl anion equivalents II. Investigations on the scope of the method: Sterically hindered and aromatic N-methylamines

Article abstract of DOI:10.1055/s-1991-26532

The scope of the methyl deprotonation of secondary methylamines protected as lithiodithiocarbamates has been investigated. Deprotonation is possible with branched N-alkylmethylamines such as the cyclohexyl derivative but failed in the case of N-tert-butylmethylamine. With aromatic methylamines such as N-methylaniline regioselective methyl- as well as ortho-deprotonation is possible depending on the base used.