Lead tetraacetate with trimethylsilyl azide

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). 

A soln. of. d -cholestene and trimethylsilyl azide in abs. methylene dichloride treated at - 20 during 1-2 hrs. with a soln. of Pb-tetraacetate in the same solvent, and allowed to warm to 20° with stirring during 15 hrs. 3a-azidocholestan-2-one. Y 50-60%. F. e. s. E. Zbiral and G. Nestler, Tetrahedron 27, 2293 (1971) reactions with lead(IV) acetate azides, review, s. Synthesis 1972, 285. 

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