Carbon fluorinated oxygen compounds

Chlorine reacts with most elements, both metals and non-metals except carbon, oxygen and nitrogen, forming chlorides. Sometimes the reaction is catalysed by a trace of water (such as in the case of copper and zinc). If the element attacked exhibits several oxidation states, chlorine, like fluorine, forms compounds of high oxidation state, for example iron forms iron(III) chloride and tin forms tin(IV) chloride. Phosphorus, however, forms first the trichloride, PCI3, and (if excess chlorine is present) the pentachloride PCI5. 

In contrast to phosphorus esters, sulfur esters are usually cleaved at the carbon-oxygen bond with carbon-fluorine bond formation Cleavage of esteri nf methanesulfonic acid, p-toluenesidfonic acid, and especially trifluoromethane-sulfonic acid (tnflic acid) by fluoride ion is the most widely used method for the conversion of hydroxy compounds to fluoro derivatives Potassium fluoride, triethylamine trihydrofluoride, and tetrabutylammonium fluoride are common sources of the fluoride ion For the cleavage of a variety of alkyl mesylates and tosylates with potassium fluoride, polyethylene glycol 400 is a solvent of choice, the yields are limited by solvolysis of the leaving group by the solvent, but this phenomenon is controlled by bulky substituents, either in the sulfonic acid part or in the alcohol part of the ester [42] (equation 29)... 

The octet rule accounts for the valences of many of the elements and the structures of many compounds. Carbon, nitrogen, oxygen, and fluorine obey the octet rule rigorously, provided there are enough electrons to go around. However, some compounds have an odd number of electrons. In addition, an atom of phosphorus, sulfur, chlorine, or another nonmetal in Period 3 and subsequent periods can accommodate more than eight electrons in its valence shell. The following two sections show how to recognize exceptions to the octet rule. 

Chlorine in its compounds with elements other than oxygen and fluorine, exhibits a negative oxidation number, 1 (rule 8, Section 16.1). Thus, the oxidation number of carbon in this compound must be positive. The maximum oxidation number of carbon in its compounds is +4 because it is in group IV. Thus, the formula is CCI4. The sum of the four (1) oxidation numbers for the chlorine atoms and the one (+4) oxidation number for the carbon atom is zero, the charge on the compound. ... 

Most of the elements found in organic compounds, such as carbon, hydrogen, oxygen, nitrogen, sulfur, phosphorus, fluorine, and iodine, have one major isotope. Chlorine and bromine, on the other hand, have two, giving characteristic patterns to the mass spectra of their compounds. 

Trifluoromethyl hypofluorite, CF3OF, is formed by the reaction of fluorine in excess with carbon monoxide, carbon dioxide, methanol, or other compounds containing both carbon and oxygen. In the procedure described below, carbon monoxide first reacts with an excess of fluorine to give largely carbonyl fluoride. The mixture is then passed through a hot tube where nearly all of the carbonyl fluoride reacts with fluorine to give trifluoromethyl hypofluorite. It is desirable to use somewhat more than two volumes of fluorine per volume of carbon monoxide. If this is not done, much perfluorodimethyl peroxide [bis(trifluoromethyl) peroxide] is formed by the combination of carbonyl fluoride with tr fluoromethyl hypofluorite by the reaction ... 

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