Cyanogen chloride, described

The preparation of chlorosulfonyl isocyanate is described in Org. Syn., Coll. Vol. 5, 226 (1973). This compound is highly corrosive, reacts explosively with water, and may be contaminated with cyanogen chloride. 

The formadon of alkynenitriles from alkynylmagnesium halides and cyanogen chloride was described far die fust tune by Grignard [114], A number of these nitriles have been prepared in our laboratory from alkynyllithium and cyanogen chloride using I O as a solvent [115], Cyanogen bromide is unsuitable because the alkynylide attacks on bromine [2],... 

Although cyanogen is a distinct molecule (below), that term sometimes is used to describe any substance that forms cyanide in the body. By this extended definition, cyanogen chloride is a cyanogen. 

The preparation of alkyl, alkenyl, and aryl derivatives of cyanoacetylene (1) poses no particular problems. In most cases a terminal acetylene is metalated or converted into an alkynyl Grignard reagent, and these intermediates are subsequently intercepted by a cyano source , which in most cases is either cyanogen chloride or bromide and sometimes cuprous cyanide or phenyl cyanate. Of course, dehydration of an acetylenic amide as described for the parent molecules is also possible and has occasionally been employed. 

The effects from cyanide poisoning are those of progressive histotoxic tissue hypoxia (Figure 10-2). The symptoms, signs, and physical findings are directly related to the dose of cyanide, the route of exposure, and the type of cyanide compound. In addition to the effects described below, cyanogen chloride also produces irritation of the eyes and... 

Cyanamide, HjNCN, has been prepared by (1) desulfurizing thiourea with mercury(II) oxide, lead acetate, or bromine, (2) passing gaseous cyanogen chloride into ammonia dissolA in anhydrous ether, and (3) oxidizing thiourea with alkaline permanganate. The method described below is an adaptation for laboratory use of a commercial procedure that uses calcium cyanamide as a starting material. 

The details of this preparation are practically the same as those given for p-tolu-nitrile (Preparation 82). A cuprous-potassium cyanide solution, prepared as therein described, is warmed to about 70°, and added in small portions to a solution of benzene-diazonium chloride prepared from 18-6 gms. (1 mol.) of aniline as described in Preparation 379. When the addition is complete, the liquid is warmed on a water bath for 15 minutes and distilled in steam the distillate is extracted with ether. The ethereal solution is washed repeatedly with dilute caustic soda and with dilute sulphuric acid, dried over anhydrous potassium carbonate, filtered, and the oil which remains on driving off the ether fractionated. Owing to the evolution of cyanogen and hydrocyanic acid, this preparation must be carried out in a good fume cupboard. 

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