The aza-Payne rearrangement: a synthetically valuable equilibration

A New Selena‐Aza‐Payne‐Type Rearrangement of Aziridinylmethyl Tosylates Mediated by Tetraselenotungstate

“…Intramolecular nucleophilic displacement of aziridines/epoxides with oxygen (Payne rearrangement), [1] nitrogen (azaPayne), [2] sulfur (thia-Payne), [1c,3] selenium [4] and tellurium allylamine derivatives as the major products and cyclic fivemembered diselenides as the minor products in good yields under mild reaction conditions without using any Lewis acid or base.…”

[1,4]Dithiepino[2,3‐b]furans from Oxiranecarbaldimines and Lithiated 1,3‐Dithiane: A Series of Rearrangement Reactions in One Pot

“…These alcohols 4 rearrange under acidic conditions to form [1,4]dithiepino[2,3-b]furans 5 with high distereoselectivity. The key step of this one-pot reaction cascade was ring expansion of the 1,3-dithiane moiety with simultaneous ring opening of the protonated aziridine.…”

“…The reaction mixture was quenched with water (10 mL), and the aqueous phase was extracted with dichloromethane (4 ϫ 15 mL). Dichloromethane was added to the organic phase until the solid was dissolved, and the combined organic phases were dried with MgSO 4 X-ray Crystal-Structure Analysis for 8: [19] …”

The [Ru(CO)(porphyrin)]‐Catalyzed Synthesis of N‐Aryl‐2‐vinylaziridines

“…The chemical stability of a vinylaziridine largely depends on the nature of the substituent on its aziridine nitrogen, [32][33][34][35] with reactivity towards nucleophiles being promoted by the presence of an electron-withdrawing group on the nitrogen atom [3,34] whereas a rearrangement frequently occurs when a N-aryl group is present in the molecule. [36,37] Organic azides [38] -in particular sulfonyl [39,40] and aryl azides [41,42] -represent a versatile class of aminating agents.…”