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Imidazol‐2‐ylidene Reactivity towards Cyanocarbons
Author(s) -
Arduengo III Anthony J.,
Calabrese Joseph C.,
Marshall William J.,
Runyon Jason W.,
Schiel Christian,
Schinnen Christoph,
Tamm Matthias,
Uchiyama Yosuke
Publication year - 2015
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201500578
Subject(s) - tetracyanoethylene , cyanation , ring (chemistry) , electrophile , chemistry , reactivity (psychology) , medicinal chemistry , imidazole , polymer chemistry , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The interaction of electron rich imidazol‐2‐ylidenes with electron poor cyanocarbons is reported. Contrary to previous reports of electron transfer products from imidazol‐2‐ylidenes and tetracyanoethylene, a number of ring forming cyanocarbon ring structures are isolated and characterized. Cyanation of the imidazole ring was explored by the addition of cyanogen chloride to imidazol‐2‐ylidenes. Backbone cyanation often occurs when hydrogen atoms are in the C‐4/5 positions. When tetrasubstituted imidazol‐2‐ylidenes are employed, 2‐cyanoimidazolium halide salts can be isolated. These salts maintain an electrophilic cyano group and are precursors to thermally stable high nitrogen content imidazolium tetrazolides.