Nitrogen as the Substituent

The basic principles of the previous section (oxygen substituent) can be transferred to nitrogen as the substituent. Here most of the examples use either potassium tert-butylate or a stoichiometric deprotonation with n-butyllithium followed by protonation with methanol. 

Propargylated tosylamides also isomerize efficiently [221, 281]. On the other hand, rare examples are propargylated hydrazines [251], N-propargylated imines [282], isonitriles (must be N-propargylated) [283], ammonium salts [284] and azides [285], 

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