The original focus of this thesis was ynol ether synthesis which was successful using simple and easy-to-prepare precursors (chloroacetylenes) but low yielding. Attention was then diverted to the design and synthesis of a range of thioynol ethers (alkynyl sulfides) utilising chloroacetylenes. The reaction of a chloroacetylene with a thiolate salt in the presence of an amine mediator (Me2NH or DMEDA) yielded the alkynyl sulfides in excellent yields. The alkynyl chlorides were easily prepared from the parent alkynes contrasting sharply with the cumbersome synthesis of an alkynyl sulfonamide previously required. As well as chloroacetylenes, bromo- and iodoacetylenes have also been studied and the differences in their reactivity are highlighted. With a successful route to thioynol ethers at hand, brief mechanistic investigations were conducted into their reactivity. Finally, preliminary studies have been carried out on the reactivity of their derivatives
