5 years ago

Arsenic-Mediated C−C Coupling of Cyanides Leading to Cyanido Arsazolide [AsC4N4]−

Arsenic-Mediated C−C Coupling of Cyanides Leading to Cyanido Arsazolide [AsC4N4]−
Jörg Harloff, Sören Arlt, Alexander Villinger, Alrik Stoffers, Axel Schulz
The chemistry of arsenic cyanides has been investigated and is found to be completely different to the chemistry of the heavier analogs antimony and bismuth as well as phosphorus. The reaction of As(CN)3 with cyanide salts resulted in the formation of an unknown cyanido arsazolide heterocycle, which represents a structure isomer of the desired [As(CN)4]−. The structure, bonding, and formation of this unusual heterocycle is discussed featuring an arsenic mediated C−C coupling of cyanides. [AsC4N4]− salts with different counterions such as [PPh4]+, [PPN]+=[Ph3P-N-PPh3]+, Ag+, and [BMIm]+ are reported with [BMIm][AsC4N4] being a low-temperature ionic liquid (Tm=−62 °C). Go get some cyanide and…isomerize: A novel [AsC4N4]− heterocycle is formed in an unusual isomerization process from its structural isomer [As(CN)4]−, which is formed as transient species when As(CN)3 is treated with CN− (see scheme). Two arsenic-mediated C−C coupling steps are necessary for the formation of the [AsC4N4]− aromatic ring system.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201703317

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