Nitrogen as Leaving Group: Aliphatic Diazonium Ions

Nitrogen is one of the best known leaving groups. Decomposition of aliphatic diazonium ions has rendered carbocations (carbon cations) accessible in cases where the solvolysis of halides or sulfonic esters follows different pathways. The limits of unassisted decomposition are seen in primary diazonium ions, where the participation of external nucleophiles and of neighboring groups in the elimination of nitrogen becomes noticeable. Cyclopropanediazonium ions occupy a position intermediate between aliphatic and aromatic diazonium ions. New versatile methods of generating aliphatic diazonium ions facilitate their preparative use.