Uses
Diiminosuccinonitrile reacts with electron-rich alkenes to form dicyanotetrahydropyrazines; it reacts with ketones to form dicyanoisoimidazoles.
Preparation
A solution of dry Triethylamine (1.5 mL) in CH2Cl2 (15 mL) is added dropwise over 45 min to a solution of Hydrogen Cyanide (20 g, 0.74 mol) and cyanogen (17.4 g, 0.34 mol) in CH2Cl2 (120 mL) at -45 to -40 °C; the reaction is mildly exothermic and DISN precipitates as the triethylamine is added; after 30 min the product is collected while still cold and washed with CH2Cl2 and ether to give 33.6 g (95%) of DISN as a fine tan powder of sufficient purity for synthetic use.
Synthesis Reference(s)
The Journal of Organic Chemistry, 37, p. 4133, 1972
DOI: 10.1021/jo00798a037
