Alkynes are an important class of compounds and are used frequently in organic synthesis. Currently, a major use lies in a growing class of reactions referred to as ‘Click Chemistry’ reactions. Unfortunately, these alkynes are often expensive or complex to synthesize, so we set out to design a synthetic method capable of forming new alkynes predictably using the decomposition of a heterocyclic ring. In this presentation we discuss the theory behind this synthetic method and show the experimental results obtained.
One method attempted included formation of a heterocyclic ring starting from an isocyanate or sulfinylimine. The decomposition of these rings resulted in formation of a carbon-nitrogen triple bond, instead of the intended carbon-carbon triple bond. Both methods have proved to be effective for producing aromatic nitriles. In addition, we examine the decomposition of cheaply-available pyrazolone rings, and 2-haloacetophenones.
