Cyanohydrin synthesis by Cyanation or …

The scope of the process is illustrated through the examples shown in . Substrates with longer alkoxy groups react smoothly (entry 1), and functional groups such as alkenes, silyl ethers, and sulfides are tolerated (entries 2–4). Ethers with branched alkoxy groups react efficiently, though little stereocontrol is observed (entry 5). The vinyl group can be lengthened (entries 6 and 7), and cyclic enol ethers react well (entry 8). These transformations illustrate the generality of cyanohydrin ether formation through Brønsted acid-mediated enol ether hydrocyanation and provide an entry into the development of an asymmetric variant.

The first synthesis of a cyanohydrin (mandelonitrile) was reported in 1832 by Winkler.

Available structural data of GMC oxidoreductases in complex with substrates, products, or inhibitors include cholesterol oxidase (CHOX) with the steroid substrate dehydroisoandrosterone (), cellobiose dehydrogenase (CBDH) in complex with the inhibitor cellobiono-1,5-lactam (), and pyranose 2-oxidase (POX) in complex with the reaction product 2-keto-β--glucose (), the slow substrate 2-fluoro-2-deoxy--glucose (), or the weak inhibitor acetate (). Superposition of these structures based on the pteridin moiety of flavin with the PaHNL1−benzaldehyde structure and mandelonitrile-bound model are shown in Figure . The structures superimpose well (at least 70% of residues within 3 Å rmsd cutoff), including the conformation of active site residues.

the mechanism of a cyanohydrin going ..

The first step of the mechanism is the addition of gaseous HCl to the cyanohydrin 1.

Chiral Brønsted acid catalysis can also be used to prepare enantiomerically enriched cyanohydrin ethers from conventional acetal precursors (). Dibenzyl acetal 45 reacts with Me3SiCN in the presence of 26 to provide (S)-2 in 85% yield and with an er of 82.5:17.5. These numbers are comparable to the values that were observed with the corresponding vinyl ether substrate. Dimethyl acetal 46 reacts under these conditions to yield (S)-17 in 91% yield and with an er of 73:27. Again these values are similar to the results in the vinyl ether series, indicating that the choice of a vinyl ether or acetal substrate should generally be dictated by synthetic accessibility since reaction outcomes are negligibly different. Acetals, however, are clearly superior substrates to poorly reactive (E)-vinyl ethers in these processes. The similarities between the outcomes of reactions with acetals and enol ethers suggests that they proceed through the same intermediates, and the acetals do not react through through a pathway in which one of the enantiotopic alkoxy groups is preferentially activated by the catalyst to generate a tight ion pair between the oxocarbenium ion and the departing alcohol. NMR studies showed that phosphoryl triflimides are silylated by Me3SiCN in the absence of phenol to form a Lewis acid that most likely serves as the active catalyst in these processes. Trimethylsilyl ethers are observed as products in these reactions in accord with this hypothesis.

Mechanism of the Strecker Synthesis

Sodium and potassium cyanides are principally prepared by the direct reaction of hydrogen cyanide with the respective alkali in closed systems (European Chemicals Bureau, 2000a,b). Sodium cyanide is also prepared to a lesser extent by melting sodium chloride with calcium cyanamide or by heating sodium amide salt with carbon.

Cyanohydrin reaction - WikiVisually

Common synonyms of acetone cyanohydrin are ACH, 2-cyano-2-propanol, 2-methyllactonitrile, and 2-hydroxy-2-methyl propanenitrile. It dissociates on standing to liberate hydrogen cyanide. Its boiling point is 120 °C (with decomposition to hydrogen cyanide and acetone). Its conversion factors in air are:


In relation to characterization of concentration–response for repeated-dose toxicity for inhalation (relevant principally to the occupational environment), in three separate studies in rats, there were no adverse systemic effects in rats exposed to acetone cyanohydrin, which is rapidly hydrolysed to hydrogen cyanide at physiological pH, at concentrations up to 211 mg/m3 (corresponding to a concentration of 67 mg hydrogen cyanide/m3). The steepness of the dose–effect curve is illustrated by the observation of 30% mortality among rats exposed part of the day to 225 mg acetone cyanohydrin/m3 (71 mg hydrogen cyanide/m3).

Mandelonitrile is the cyanohydrin from benzaldehyde

Sodium cyanide is extensively employed in a large number of industrial processes, including electroplating and case-hardening of metals; the extraction (cyanidation) of gold and silver from ores; base metal flotation; coal gasification; and the fumigation of ships, railroad cars, buildings, grain silos, flour mills, seeds in vacuum chambers, and soil. Large quantities of sodium cyanide are used to introduce cyano groups into organic compounds, in particular through a reaction with organic halogen compounds to yield nitriles. The nitriles can then be converted to a variety of carboxylic acids, amides, esters, and amines. Potassium cyanide is used for electrolytic refining of platinum, for metal colouring, and as an electrolyte for the separation of gold, silver, and copper from platinum (Eisler et al., 1999; Patnaik, 1999; ACGIH, 2001; ECETOC, 2004). Cyanide salts are used as chelating agents, and the complex cyanides of copper, zinc, and cadmium are used in electroplating processes, principally the plating of iron, steel, and zinc (ECETOC, 2004).