Abstract
Starting from N,N,N′,N′,N′′,N′′-hexaalkylguanidinium chlorides and terminal alkynes, a series of new orthoamide derivatives of alkynecarboxylic acids were prepared. The orthoamides were converted into propiolamidinium chlorides by reaction with benzoyl chloride and into propiolamidinium triflates by reaction with triethylsilyl trifluoromethanesulfonate. Propiolamidinium salts undergo conjugate addition reactions with sec-amines and thiols. Treatment of terminal alkyne chlorides with silver(I) oxide afforded a silver complex, which can apparently adopt the composition of either a bisalkynyl silver complex [Ag(CCC(NMe2)2)2]AgCl2 or a monoalkynyl silver complex [ClAgCCC(NMe2)2].
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