A convenient one‐pot synthesis of unsymmetrical sulfamides via a Lossen‐like rearrangement is reported. The protocol operates under simple conditions at room temperature and does not require an inert atmosphere and a dry solvent. The ability of N‐hydroxy arenesulfonamide O‐derivatives to generate under mild conditions N‐sulfonylimine intermediates was a trigger point for developing a general synthetic strategy towards unsymmetrical sulfamides. The synthetic potential of the methodology has been investigated by preparing cyclic sulfamides and new potential chiral organocatalysts.magnified image

No abstract

No abstract

Abstract4-Cyano-3-oxotetrahydrothiophene (c-THT) has much more to offer than just a platform to various heterocyclic scaffolds. This solid, bench-stable and commercially available reagent can be readily transformed into thioglycolic acid and acrylonitrile upon simple addition of a hydroxide anion. This interesting feature enables its use as a particularly versatile acrylonitrile anion surrogate.

A direct synthesis of unsymmetrical sulfamides is achieved by Et3N‐promoted reaction of N,O‐bissulfonyl hydroxylamines with primary amines or diphenylamine.