Lead phenyliododiacetate

Trimethylsilyl azide, (TMSN3) reacts with carbon-carbon double bonds to form a compound which can be cleaved by lead tetraacetate (or phenyliododiacetate) to yield a carbonyl and a nitrile, as in equation (37).The reagent has been tqrplied extensively to the cleavage of unsaturated steroids, as illustrated in equation (38). 

Maleic diamide has been cyclized by strong oxidants, lead tetraacetate, or phenyliododiacetate to substituted uracils in high yield (27RTC268 90AJC451) Scheme 14). 

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