Hydrogen cyanide reaction with

The enhanced reactivity of fluoroalkyl ketones is also manifested in the failure to stop the reaction with hydrogen cyanide at the stage of cyanohydrins Instead, oxazohdinones or dioxolanones are formed (equation 11) If, however, the reaction IS conducted under basic conditions with sodium bisulfite and sodium cyanide, the desired cyanohydrin can be prepared [ll ... 

The preparation of a formyl-substituted aromatic derivative 3 from an aromatic substrate 1 by reaction with hydrogen cyanide and gaseous hydrogen chloride in the presence of a catalyst is called the Gattermann synthesis This reaction can be viewed as a special variant of the Friedel-Crafts acylation reaction. 

Until the 1960s, acrylonitrile was, like vinyl acetate, made from acetylene (by reaction with hydrogen cyanide), but research on catalysts in the 1950s led to the much less costly route shown above. 

Huthmacher, K. Krill, S. Reactions with Hydrogen Cyanide (Hydrocyanation). In Applied Homogeneous Catalysis with Organometallic Compounds Cornils, B., Herrmann, W. A., Eds. VCH Weinheim, Germany, 1996 pp 465-486. 

In ethereal solution diazomethane can he preserved for a long time. Information about its numerous reactions (with hydrogen cyanide, acetylene, quinone, etc.) can he found in the special literature of the subject. As has already been mentioned, it is an important methylating agent, especially for phenols. With them it reacts in such a way that the two nitrogen atoms are eliminated as elementary nitrogen, and the two valencies which thus become free are occupied by H and OR. 

Acrylonitrile was made completely from acetylene in 1960 by reaction with hydrogen cyanide. For some years ethylene oxide was the raw material for addition of HCN and elimination of H2O. 

Norepinephrine Norepinephrine, L-l-(3,4-dihydroxyphenyl)-2-aminoethanol (11.1.4), is synthesized by two methods starting from 3,4-dihydroxybenzaldehyde. According to the first method, the indicated aldehyde is transformed into the cyanohydrin (11.1.3) by reaction with hydrogen cyanide, which is then reduced into norepinephrine (11.1.5) [11,12]. 

Acrylonitrile (2-propenonitrile, propene nitrile, vinyl cyanide, CH2=CHCN freezing point -83.5°C, boiling point 77.3°C, density 0.806) used to be manufactured completely from acetylene by reaction with hydrogen cyanide. 

Huthmacher, K. Krill, S. Reactions with hydrogen cyanide (hydrocyanation). 

When the bifunctional reactant is aldehyde (glutaraldehyde), cyanopiperidines 119 (Fig. 43) are obtained by reaction with hydrogen cyanide and primary amine, although one of the nitrile groups may be partially hydrolyzed to amide during the synthesis. ... 

SAFETY PROFILE Poison by subcutaneous, intravenous, and intramuscular routes. Moderately toxic by other routes. A severe eye irritant. Mutation data reported. Explosive reaction with potassium chlorate or bromine trifluoride. Violent reaction (ignition) with bromine pentafluoride, NH4, NO3, and IF7. Reaction with hydrogen cyanide may give the explosive nitrogen trichloride. When heated... 

Aromatic aldehydes react with sodium hydrogen sulfite to yield bisulfite compounds. Further reaction with sodium cyanide forms the hydroxynitrile (cyanohydrin), which can sometimes be formed directly from the aldehyde by reaction with hydrogen cyanide (Scheme 6.11). 

Aromatic aldehydes generally do not produce cyanohydrins on reaction with hydrogen cyanide, but undergo the benzoin condensation (Scheme 6.12). The initial product from nucleophilic attack by cyanide ion is depro-tonated to form a resonance-stabilized carbanion, which attacks a second molecule of the aldehyde. Elimination of HCN leads to an a-hydroxy ketone, benzoin (2-hydroxy-1,2-diphenylethanone). The benzoin condensation is catalysed specifically by cyanide ion, which assists in both the formation and stabilization of the carbanion. The reaction is limited to aromatic aldehydes, since the aryl ring also stabilizes the anion. 

By the reaction with hydrogen cyanide, HCN, forming cyan-hydrines, which are acid nitriles, with hydroxyl amine, H2NOH, forming oximes, and with phenyl hydrazine, H2N—NH—CeHs, forming hydrazones, all of which reactions are characteristic of the carbonyl group, carbohydrates in water solution are aldehyde or ketone compounds. 

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