Phosphorodiamidates alcohols

In view of the rapid toxic action and myotic effect of the dialkyl phosphorofluoridates and of the high toxicity of some of the phosphorodiamidic fluorides, we prepared2 and examined a hybrid molecule containing the essential features of each type of compound. The first to be examined was ethyl phenyl-phosphoramidofluoridate (VII). One mol. of phosphorus oxy-dichlorofluoride was added to 1 mol. of ethyl alcohol, and the resulting ethyl phosphorofluoridochloridate (which it was not necessary to isolate) was treated with aniline. 

SYNS 2-(BIS(2-CHLOROETHYL)AMINO)TETRA-HYDROOXAZAPHOSPHORINE CYCLOHEXYLAMINE SALT NJ4-BIS(2-CHLOROETHYL)-N -(3-HYDROXY-PROPYL)PHOSPHORODIAMIDATE, CYCLOHEXYL-AMMONIUM SALT N,N-BIS(2-CHLOROETHYL)-N -3-PHOSPHORODIAMIDIC ACID HYDROXYLPROPYL-CYCLOHEXYLAMINE SALT CYTOXYL ALCOHOL CYCLOHEXYLAMMONIUM SALT NCI-C04922 NSC-52695... 

Lithium ethylamineltert-butyI alcohol Hydrocarbons from phosphorodiamidates... 

The mechanism of these reactions is assumed to involve displacement of chloride by the carboxylate anion to give a phospho-rodiamidate (eq 4). Subsequent nucleophilic attack of an alcohol, amine, or a carboxylate anion affords phosphorodiamidic acid and esters, amides, and anhydrides, respectively (eq 5). 

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