Tetraselenotungstate 1 reacts with simple (N-tosylaziridinyl)-methyl tosylate derivatives to give allylamine derivatives as the only products by an unprecedented selena-aza-Paynetype rearrangement. When the methodology is extended to disubstituted (N-tosylaziridinyl)methyl tosylates, regio-and stereospecific ring-opening of the aziridines occurs to afford
Aziridinemethanol sulfonate esters react with tetrathiomolybdate 1 to give thiirane derivatives as the major product and cyclic disulfides as minor product under mild reaction conditions via an unprecedented thia-aza-Payne-type rearrangement. Interestingly, when the reaction of 1 was carried out with 2-aziridino-cyclohexanol derivatives it resulted in the formation of thia-bicyclo[3.1.1]heptane or dithia-bicyclo[3.2.1]octane derivatives.
Tetrathiomolybdate Mediated Rearrangement of Aziridinemethanol Tosylates: A Thia-aza-Payne Rearrangement. -The rearrangement affords thiiranes. 5-Membered cyclic disulfides are also formed. Starting from the tosylates (IV) and (VIc), however, only disulfides are obtained. Bicyclic aziridines are not able to undergo thia-aza-Payne rearrangement. The derivative (XII) exclusively provides the disulfide (XIII) and the analogue (XIV) yields the unexpected sulfide (XV). -(SURESHKUMAR, D.; KOUTHA, S. K.; GANESH, V.; CHANDRASEKARAN*, S.;
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.