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Introduction to Phosphorus Analogs of Amines

Phosphines are the phosphorous analogs of amines. The chemistry of phosphines and the associated phosphite esters is dominated by their strong nucleophilicity and reducing character. The nucleophilicity of the trivalent phosphorus results in quick formation of phosphonium salts when such type of compounds is treated with reactive alkyl halides. For an instance, even though resonance delocalization of the nitrogen electron pair in triphenylamine, (C6H5)3N, renders it comparatively unreactive in SN2 reactions, the subsequent phosphorus compound, triphenylphosphine, goes through a quick and exothermic reaction to give a phosphonium salt, as displayed below in the first equation. Phosphite esters react in similar way, but the resulting phosphonium salts (shaded box) are frequently unstable, and on heating yield dialkyl phosphonate esters by way of a second SN2 reaction (equation 2 below).

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Oxidation States of Phosphorus Compounds

The dissimilarity in oxidation states between phosphorus and nitrogen is less pronounced than between sulfur and oxygen. Organophosphorus compounds having phosphorus oxidation states ranging from -3 to +5, as displayed in the table, are well known (some simple inorganic compounds are displayed in green color in the diagram). Like in the example of sulfur, the P=O double bonds displayed in some of the formulas do not contains the customary sigma & pi-orbitals found in carbon double bonds. Phosphorus is a element of third row, and has five empty 2d-orbitals that may be employed for p-d bonding in a fashion identical to p-p (π) bonding. In this fashion phosphorus may expand an argon-like valence shell octet by two electrons (example phosphine oxides).

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Phosphorus Compounds as Reducing Agents

Trivalent phosphorus is simply oxidized. In difference with amines and ammonia, phosphine and its mono and dialkyl derivatives are pyrophoric, bursting into the flame on contact with the oxygen in air. The affinity of trivalent phosphorus for oxygen (and sulfur) has been put to make use of in several reaction systems, three of which are displayed here. The triphenylphosphine oxide formed in reactions 1 & 3 is a very stable polar compound and in several cases it is simply removed from the other products. Reaction 2 is a usual formulation of the useful Corey-Winter technique for converting vicinal glycols to alkenes.

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Triphenylphosphine is also oxidized by halogens and with bromine yields dibromotriphenylphosphorane, a crystalline salt-type compound, helpful for converting alcohols to alkyl bromides. Like in a number of earlier illustrations, the formation of triphenylphosphine oxide in the irreversible SN2 step presents a thermodynamic driving force for the reaction.

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