Trimethylsilyl cyanide → HCID 20225962, compound

Participants

Reaction Steps

A solution of chloro bis(2-fluoro-2,2-dinitroethoxy)methane (2.45, 6.9 mmol) prepared in example 2 and cyanotrimethylsilane (0.77 g, 7.8 mmol) in 15 ml of dichloroethane was refluxed for 40 hours. NMR analysis showed consumption of the chloroformal and the presence of the cyanoformal together with a small amount of 2-fluoro-2,2-dinitroethyl formate. A 2.45 g residue from concentration of the reaction solution on a rotary evaporator was chromatographed on Silica Gel 60 (70-230 mesh, 25 g) with a 3:2 solvent mixture of hexanes/dichloromethane to give 1.51 g (63%) of bis(2-fluoro-2,2-dinitroethoxy)acetonitrile: mp 41°-2°; IR (film) 2260 (CN, weak) cm-1 ; 1H NMR (CDCl3): δ5.67 (s,l), 4.87 (d, 4, J=16 Hz); mass spectrum (CI, CH4), m/z (rel intensity): 386 (M+41, 3), 375 (M+30, 2), 319 (100 ), 92 (50).

Provenance & Evidence