The Reactions of Dialkyl Phosphites and Phosphine Oxides with Iodosylbenzene

The reaction of iodosylbenzene with >P(O)H type of acids (dialkyl phosphites, secondary phosphine oxides) was studied. The acids of >P(O)H type add to iodosylbenzene to yield intermediate 6 which in the aprotic solvents yields oxidation products, it means >P(O)OH acids and/or anhydride of >P(O)OP(O)< type. On the other hand if the reaction is performed in alcohol as a solvent in the presence of sodium alcoholate >P(O)OR ester is the major product.