CARBONYL CYANIDE

Single-Carbon Insertion Reactions. Carbonylation, cyanidation, and "DCME," and related reactions are convenient general processes developed to bring about the transfer of organic groups from boron to a siagle-carbon atom. 

Hydroboration of a,C0-dienes with monoalkylboranes gives reactive organoboron polymers which can be transformed into polymeric alcohols or polyketones by carbonylation, cyanidation, or the DOME reaction followed by oxidation (446—448). 

With substances that give up an electron more readily than aromatic hydrocarbons, such as potassium, nickel carbonyl, cyanide ion, or iodide ion, complete transfer of an electron occurs and the TCNE anion radical is formed (11). Potassium iodide is a particulady usefiil reagent for this purpose, and merely dissolving potassium iodide in an acetonitrile solution of TCNE causes the potassium salt of the anion radical to precipitate as bronze-colored crystals. 

With pyridine, reaction takes place at the nitrogen rather than at a double bond, and an yUd [27032-01-5] is formed (57,58). Sulfides react similarly to give sulfOidenes and carbonyl cyanide (59). 

This is the most convenient synthesis of carbonyl cyanide [1115-12-4]. The product of (8) and dimethyl sulfide is dimethyl sulfonium dicyanomethyUde... 

Carbonyl cyanide-p-trifluoro-metho5 henyl hydrazone... 

In addition to direct inhibition of the vesicular transport protein, storage of neurotransmitters can be reduced by dissipation of the proton electrochemical gradient. Bafilomycin (a specific inhibitor of the vacuolar H+-ATPase), as well as the proton ionophores carbonyl cyanide m-chlorophenylhydrazone (CCCP) and carbonylcyanide p-(trifluoromethoxy) phenylhy-drazone (FCCP) are used experimentally to reduce the vesicular storage of neurotransmitters. Weak bases including amphetamines and ammonium chloride are used to selectively reduce ApH. 

Paul We have been talking about the SR as a site of release, as if it were one thing. There is superficial SR, deep SR and ER, with three different ryanodine receptor isoforms and at least two different SERCAs. Are these on the same vesicles, or different vesicles What s the role of the ER Do they communicate with one another There are a lot of questions about this compartmentalization and vectorial release. The mitochondria also intrigue me the SR can still function quite well after CCCP (carbonyl cyanide ///-chlorophenylhydrazone), which inhibits mitochondrial Ca2+ uptake. 

McCarron Yes, uncouplers increase the depolarization of evoked Ca2+ transients and slow the rate of decay. This was with CCCP (carbonyl cyanide ///-chloro-phenylhydrazone). 

Benz, R. and McLaughlin, S. (1983). The molecular mechanism of action of the proton ionophore FCCP (carbonyl cyanide p-trifluoromethoxyphenylhydrazone), Biophys. J., 41, 381-398. 

Carbon tetrachloride-organo-phosphine, chlorides from alcohols with, 54, 63 CARBONYL CYANIDE, 51, 70 Carbonyl cyanide, with alcohols, 51, 72... 

Kopp S, Kisling G, Paulson D, et al. 1989. Cardiac actions of cadmium, potassium cyanide and carbonyl cyanide m-chlorophenylhydrazone [Abstract]. FASEB J 3 A-251. 

LeCloirec A, Best SP, Borg S, et al. 1999. A di-iron dithiolate possesing structural elements of the carbonyl/cyanide sub-site of the H center of Fe-only hydrogenase. Chem Commun 22 2285-6. 

Determination of the structure of an iron-sulfur-carbonyl-cyanide hydrogenase" " has been complemented by the synthesis and structural characterization of model compounds (Et4N)2 [Fe(SPh)2(CN)2(CO)2]," (299)and related species in which the sulfur-bridging is provided by the tripodal thioether MeSCFl2C(Me)(CH2S)2." ... 

Caution Carbonyl cyanide and water react with explosive violence to form hydrogen cyanide and carbon dioxide. This preparation should be carried out in a good hood with shielding, and rubber gloves should be worn. 

The procedure described is that of Linn, Webster, and Benson.3 Carbonyl cyanide has previously been prepared by the pyrolysis of the diacetyl derivative of diisonitrosoacetone, a multistep process that suffers from low yield, lack of reproducibility, and risk of explosion.2 The present procedure provides a convenient high-yield synthesis of carbonyl cyanide. 

Tetracyanoethylene oxide, with n-butyl sulfide to give carbonyl cyanide,... 

The diethyl phthalate is freed of traces of water and ethanol by distilling about 5% of it under reduced pressure, b.p. 185° (20 mm.) and then cooling the residue with protection from moisture. Moisture must be excluded because carbonyl cyanide reacts vigorously with water. 

The distillate is treated with tetracyanoethylene oxide to remove the small amount of w-butyl sulfide that codistills with carbonyl cyanide. 

Gas chromatographic analyses of various cuts indicate essentially pure carbonyl cyanide with traces of hydrogen cyanide and carbon dioxide. Both are hydrolysis products of carbonyl cyanide and probably are formed because of traces of moisture on the column. 

These occur readily between electron-rich alkenes and electron-poor carbonyl compounds. The first example, reported in 1959 (64HC(19-2)729), was the formation of 4,4-diaryloxetane-2,2-dicarbonitriles by the room temperature reaction of 1,1-diarylethylenes and carbonyl cyanide. Continued investigation of this reaction shows that a telomerization product is also formed, the tetraphenylpentadienedinitrile (55) from 1,1-diphenylethylene and carbonyl cyanide. This may be interpreted to indicate that carbon-carbon bond formation may commence somewhat ahead of carbon-oxygen bond formation (75MI51302). This... 

Carbonyl cyanide reacts readily with ketene and dialkylketenes to give the corresponding dicyano-/3-lactones (equation 109). This reaction seems entirely analogous to the addition of carbonyl cyanide with alkenes to give oxetanes, described in the preceding section (75MI51302). 

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