Abstract
Diethyl p-tolylthioethynylphosphonate (10) was synthesized from diethyl ethynylphosphonate (7) by two routes and oxidised to the corresponding sulphoxide (11) and sulphone (12). The sulphone showed no triple bond i.r. absorption, but a strong Raman band, and nucleophiles could add to either end of the triple bond. These alkynes gave indolizines with pyridinium-1-dicyanomethylides and Diels–Alder adducts with anthracenes. The orientations of the additions were deduced from 1H, 1H; 31P, 1H; and 31P, 13C coupling constants.
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