Amines carbonyl chloride fluoride

Although the most extensively recorded aspect of phosgene chemistry is its interaction with compounds at a nitrogen centre, only three reactions of carbonyl chloride fluoride with amines have been reported. No reports have appeared concerning the reactions of COCIF with tertiary amines, amino acids, hydrazine derivatives, imino compounds or nitrogen-containing heterocycles, to name but a few unstudied reagents. 

Treatment of a thiol or thiophenol with carbonyl chloride fluoride in the presence of a tertiary amine (in an inert solvent such as heptane) results in the formation of the corresponding thiol fluoroformate in 75-85% yield [1555a] ... 

Chlorodifluoroamine has been prepared by reaction of difluoro-amine with boron trichloride,1 phosgene (carbonyl chloride),2 or hydrogen chloride 2 treating a mixture of sodium azide and sodium chloride with fluorine 3 reaction of chlorine trifluoride with ammonium fluoride 4 reaction of chlorine with diflu oro-amine in the presence of potassium fluoride 5 and photolysis of tetrafluorohydrazine and sulfinyl chloride (thionyl chloride).6... 

HETEROCYCLES Copper phcnylace-tylide. Dichlorobis(benzonitrile)palladium. N-Dichloromethylene-N,N-dimcthylammo-nium chloride. Diiminosuccinonitrile. Dimethyl acetylenedicarboxylate. Dipotassium cyanodithioimidocarbonate. Ethoxy-carbonyl isothiocyanate. Ethyldiisopropyl-amine. Ethylene oxide. Hydrogen fluoride. Isocyanomethane-phosphoric acid diethyl ester. Lead tetraacetate. Lithium aluminium hydride. Methylhydrazine. Phosphoryl chloride. Polyphosphate ester. Polyphosphoric acid. Potassium amide. Potassium hydroxide. Tolythiomethyl isocyanide. Tosylmethyl isocyanide, Trichlo-romethylisocyanide dichloride. Trimethyl-silyldiazomethane. 

Carbon suboxide, 52 Carbonylation, 148, 149, 216 Carbonyl chlorofluoride, 48, 54 Carbonyl cyanide, 60-61 N,N -Carbonyldiimidazole, 61 1,1-Carbonyldi-l,2,4-triazole, 61 N-Carbonylsulfamic acid chloride (N-Carbonylsulfamyl chloride), 61 Carboxamides, 270 Carboxamine-N-sulfochlorides, 70 p-Carboxybenzenediazonium chloride, 62 p-Carboxybenzenesulfonazide, 62 Carboxylation, 15, 16 Carboxylic acid anhydrides, 133 Carboxylic acid N,N-dimethylamines, 153 Carboxylic anhydrides, 409-410 p-Carboxyphenylhydrazones, 62 Cardenolides, 130, 131 (S-Carotene, 19 /-Carvone, 451, 452 i//-Caryophyllene, 149, 150 Catechol, 65, 233 Catechol amines, 159 Catechyl phosphorus tribromide, 63 Catechyl phosphorus trichloride, 63 Cis-Cecropia juvenile hormone, 261 Cedrene, 234, 235 a-Cedrene, 349 /3-Cedrene, 349 Cendranoxide, 234, 235 Cephalosporin C, 48 Ceric ammonium nitrate, 63-65 Ceric sulfate. 65 Cesium fluoride, 346 trans-Chalcone oxide, 422 Chalcone phenylhydrazones, 257, 258 Chalcones, 406 Chloramine, 65-66, 69 Chloranil, 66-67, 113, 116, 401,454... 

One class of reaction evidently missing from this list is the reaction of sulfenes with electrophiles. Sulfene itself is strongly electrophilic and this class may be expected to be small. One class of reaction formally involving a sulfene and an electrophile is the cycloaddition with chloral and related carbonyl compounds. Evidence has been obtained for the importance of tertiary amines in this process and, as is discussed in Section V.B.5, it is unlikely that it is a simple reaction of a sulfene with an electrophile. The reaction of (trimethylsilyl)methanesulfonyl chloride with cesium fluoride in the presence of bromine... 

Detection of certain types of compounds (for example, of an aromatic skeleton). If the compound trasmits radiation (b < 1) between 220 and 800 nm, it may well be an aliphatic or alicyclic hydrocarbon, amine, nitrile, alcohol, ether, alkyl chloride, or alkyl fluoride, but the presence of conjugated double bonds, the carbonyl group, nitro group, bromine, or iodine is excluded. The detection of the aromatic nucleus in an unknown sample is carried out by measuring the absorption in the ultraviolet region of ethanolic, cyclohexane, or /i-hexane solutions of various concentrations (10 -10 mole/liter). 

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