Diazaphospholidine oxides rearrangement

Buono and co-workers showed that (aryloxy)diazaphospholidine oxides suffer [1,3] P-O to P-C rearrangement, i.e. migration of the phosphine moiety from the oxygen to the ortho carbon upon treatment with strong bases such as LDA. For instance, treatment of compound 12 with LDA followed by an aqueous work-up allowed the isolation of the o-hydroxyphenyl diazaphospholidine oxide 13 in 94% yield (Scheme 3.6). ... 

The high yields and the flawless stereoselectivity of this rearrangement prompted the preparation of several o-hydroxyaryl diazaphospholidine oxides. 

This class of compounds is interesting because of its bifunctional character, displaying both an acidic OH and a basic phosphoryl group. Table 3.7 lists the o-hydroxy diazaphospholidine oxides prepared via P-0 to P-C rearrangement. 

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