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Dilithiation Reactions Of N-Substituted Benzylamines, Richard Patrick Franks
Dilithiation Reactions Of N-Substituted Benzylamines, Richard Patrick Franks
Theses & Honors Papers
N-Cyclohexyl -2-methylbenzylamine was metalated with two equivalents of n-butyllithium activated with one equivalent of tetramethylethylenediamine (T.M.E.D.A.) , and the solvent system, time, and temperature were varied to establish a maximum yield . It was experimentally found that a thirty minute ice-water bath metalation in diethyl ether, followed by a fifteen minute condensation with benzophenone in refluxing diethyl ether gave the best yield with the benzophenone electrophile. The product was characterized by N.M.R. and found · to be 2- ( cyclohexylamino)-2-(2-toluyl ) -1 ,1-diphenylethanol (the benzylic adduct) in a 29% yield.
When N-cyclohexyl -2-methylbenzylamine was metalated for three hours in an …