Affiliation:
1. Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada
Abstract
(Bromoethynyl)benzene dissolved in hexane reacts with 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes) to produce the acetylenic amidinium salt [Ph-C≡C-IMes][Br]. Treatment of the bromide salt with KPF6 then results in the isolation of solid [Ph-C≡C-IMes][PF6]. Both salts have been characterized spectroscopically and their structures determined using X-ray crystallography. Crystals of a hydrolysis product were also isolated from this reaction on one occasion and its structure is reported. This led us to explore the reactivity of the bromide salt further. It was found to react rapidly with sodium azide (NaN3), azidotrimethylsilane ((CH3)3Si-N3), cyanotrimethylsilane ((CH3)3Si-CN), and also with IMes. All of the addition products have been characterized using X-ray crystallography.
Funder
Natural Sciences and Engineering Research Council of Canada
Canada Foundation for Innovation
Saint Mary's University
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis