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High‐Performance Isocyanide Scavengers for Use in Low‐Waste Purification of Olefin Metathesis Products
Author(s) -
Szczepaniak Grzegorz,
Urbaniak Katarzyna,
Wierzbicka Celina,
Kosiński Krzysztof,
Skowerski Krzysztof,
Grela Karol
Publication year - 2015
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201500784
Subject(s) - scavenger , chemistry , isocyanide , ruthenium , catalysis , metathesis , olefin fiber , organic chemistry , ether , olefin metathesis , combinatorial chemistry , silica gel , polymerization , polymer , radical
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.