Phosphorus Iodide related reagents

Several methods for the preparation of the parent compound in this system, tris(trimethylsilyl)phosphite, have been reported.114 118 The application of this and related reagents in reaction with alkyl halides has been reported and used for the preparation of a variety of phosphonic acid analogues of phospholipids.114119-124 Interestingly, alkyl chlorides appear to be more reactive with the silyl reagents than do alkyl iodides, a reversal of the normally observed trend with alkyl esters of the phosphorus acids. (The particular use of silyl phosphorus reagents for the synthesis of biologically significant compounds has... 

Iodides can be made smoothly from tosylates or bromides by reaction with sodium iodide in acetone.There are also several procedures based on phosphorus reagents which are mechanistically related to those discussed for bromides and chloride. One procedure involves preparation of a cyclic phosphite ester from the alcohol and c -phenylenephosphorochloridite. Treatment of the cyclic phosphite with iodine then generates the alkyl iodide.An alkoxyphosphonium intermediate is involved. 

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