Mechanism of anodic cyanation

Anodic oxidation of cyclohexene in the presence of cyanide ion

“…Isolation of the various products was performed using preparative VPC techniques. Besides 3-methoxycyclohexene (1) and dimethoxymethylcyclopentane (2), 3-isocyanocyclohexene (3), 2-cyclohexene-1 -carbonitrile (4), isocyanocyclohexane (5), cyclohexanecarbonitrile (6), and trans-2-methoxycyclohexanecarbonitrile (7) were found together with bis-2-cyclohexen-l-yl (8) and unidentified minor components. Traces of methoxycyclohexane and trans-l,2-dimethoxycyclohexane were also noted.…”

“…An Example of Kinetic Runs. Ten samples, prepared by the method described above, were heated at 70 ± 1 °C for 3,6,10,15,20,30,37,45,60, and 75 min. The reaction mixtures were submitted to GLC analysis.…”

“…The amount of indoline and indole was measured by the use of a 2 m X 6 mm stainless steel column packed with 10% diethylene glycol succi-nate on Diasolid L and dibenzyl ether as an internal standard.Other transfer hydrogenolyses were carried out in a similar way.An Example of Kinetic Runs. Ten samples, prepared by the method described above, were heated at 70 ± 1 °C for 3,6,10,15,20,30,37,45,60, and 75 min. The reaction mixtures were submitted to GLC analysis.…”

Expedient Access to Cyanated N‐Heterocycles by Direct Flow‐Electrochemical C(sp2)−H Activation

“…[35,36] In 1977, Yoshida and co-workers described the first regiospecific anodic cyanation of pyrroles and indoles using sodium cyanide. [37,38] This method, and the few others that were reported around that time, were not general nor practical, [39][40][41] and it wasn't until Goossen reported a more general approach in 2018 that interest in electrochemical cyanations resurged. [42] Although effective and straightforward, Goossen's methodology requires large excess of sodium cyanide and lacks selectivity when it comes to the varying electron density of the arene substrates.…”

Hydrogen cyanide chemistry. IV. Diiminosuccinonitrile reactions with nucleophiles, acyl halides, and carbonyl compounds

“…The only products isolated were ammonium chloride and ethyl carbamate. Reaction of sulfur with C12DISN in dimethylformamide gives 3,4-dicyano-l,2,5-thiadiazole (33).11 Thi- (9) Prepared from DAMN and COCI2: D. W. Woodward, U. S. Patent A study of the chemical reactivity of isoimidazole 35 shows that it is considerably less reactive than DISN. For example, while only a catalytic amount of sodium ethoxide in ethanol is necessary to replace the cyano groups of DISN, we have found that 35 must be treated The condensation of DISN with ketones and ketals to give dicyanoisoimidazoles is by no means a general reaction.…”