title: High-Performance Isocyanide Scavengers for Use in Low-Waste Purification of Olefin Metathesis Products.
abstract: Three isocyanides containing a tertiary nitrogen atom were investigated for use as small-molecule ruthenium scavenging agents in the workup of olefin metathesis reactions. The proposed compounds are odorless, easy to obtain, and highly effective in removing metal residues, sometimes bringing the metal content below 0.0015 ppm. The most successful of the tested compounds, II, performs very well, even with challenging polar products. The performance of these scavengers is compared and contrasted with other known techniques, such as silica gel filtration and the use of self-scavenging catalysts. As a result, a new hybrid purification method is devised, which gives better results than using either a self-scavenging catalyst or a scavenger alone. Additionally, isocyanide II is shown to be a deactivating (reaction quenching) agent for olefin metathesis and superior to ethyl vinyl ether.
authors.affiliation: Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02-089, Warsaw, Poland. szczepaniak.grzegorz@gmail.com.
authors.forename: Grzegorz
authors.identifier: http://orcid.org/0000-0002-0355-9542
authors.initials: G
authors.lastname: Szczepaniak
authors.affiliation: Apeiron Synthesis, Duńska 9, 54-427, Wrocław, Poland.
authors.forename: Katarzyna
authors.identifier: http://orcid.org/0000-0002-1807-5364
authors.initials: K
authors.lastname: Urbaniak
authors.affiliation: Apeiron Synthesis, Duńska 9, 54-427, Wrocław, Poland.
authors.forename: Celina
authors.identifier: http://orcid.org/0000-0003-3741-9617
authors.initials: C
authors.lastname: Wierzbicka
authors.affiliation: Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02-089, Warsaw, Poland.
authors.forename: Krzysztof
authors.identifier: http://orcid.org/0000-0003-3312-1602
authors.initials: K
authors.lastname: Kosiński
authors.affiliation: Apeiron Synthesis, Duńska 9, 54-427, Wrocław, Poland.
authors.forename: Krzysztof
authors.identifier: http://orcid.org/0000-0001-7126-7595
authors.initials: K
authors.lastname: Skowerski
authors.affiliation: Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02-089, Warsaw, Poland. karol.grela@gmail.com.
authors.forename: Karol
authors.identifier: http://orcid.org/0000-0001-9193-3305
authors.initials: K
authors.lastname: Grela
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D008697:Methane / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D012428:Ruthenium / Q000737:chemistry / Q000302:isolation & purification; D012822:Silicon Dioxide / Q000737:chemistry; D014866:Waste Products
chemical_list: D000475:Alkenes; D003486:Cyanides; D014866:Waste Products; D012822:Silicon Dioxide; D012428:Ruthenium; D008697:Methane
keywords: isocyanides; metathesis; olefins; ruthenium; scavengers