Tetrazolo sulfide

The architecturally novel macrolide (+)-zampanolide was synthesized in the laboratory of A.B. Smith. The C8-C9 ( )-olefin moiety was constructed using the Kocienski-modified Julia oleHnation. The required PT-sulfone was prepared from the corresponding primary alcohol via a two-step protocol employing sequential Mitsunobu reaction and sulfide-sulfone oxidation. The primary alcohol and two equivalents of 1-phenyl-1 H-tetrazolo-5-thiol was dissolved in anhydrous THF at 0 °C and treated sequentially with triphenylphosphine and DEAD. The desired tetrazolo sulfide was isolated in nearly quantitative yield. 

These salts can react with a variety of nucleophiles including amines (to afford amidines), alcohols (to afford esters), hydrogen sulfide (to afford thioamides), and isotopically labeled water (to afford 0-labeled amides). Iminium triflates are also excellent intermediates for the preparation of assorted heterocycles. Iminium triflates react with azides (to afford tetrazoles), -mercaptoamines (to afford thiazolines), and triols (to afford orthoesters) (eq 58). The reaction of lactams with Tf20 and sodium azide affords tetrazolo-fused bicyclics. ... 

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