A Convenient Synthesis and Some
Characteristic Reactions of Novel Propiolamidinium Salts

Werner Weingärtner; Willi Kantlehner; Gerhard Maas

doi:10.1055/s-0030-1258353

PAPER

A Convenient Synthesis and Some Characteristic Reactions of Novel Propiolamidinium Salts

Werner Weingärtner^a, Willi Kantlehner^b, Gerhard Maas*^a
^a Institute of Organic Chemistry I, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
Fax: +49(731)5022803; e-Mail: gerhard.maas@uni-ulm.de;
^b Faculty of Chemistry, Organic Chemistry, University of Applied Research Aalen, Beethovenstraße 1, 73430 Aalen, Germany
Fax: +49(7361)5762250; e-Mail: willi.kantlehner@htw-aalen.de;

Abstract

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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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