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 ].
Key words
alkynes - amidinium salts - orthoamides - hexamethylguanidinium
chloride - silyl triflates
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