ChemInform Abstract: Gold‐Catalyzed Synthesis of 3‐Pyrrolidinones and Nitrones from N‐Sulfonyl Hydroxylamines via Oxygen‐Transfer Redox and 1,3‐Sulfonyl Migration.

Abstract

Gold‐catalyzed reactions of N‐sulfonyl hydroxylamines with terminal alkyne lead to 3‐pyrrolidinones (II) by means of an intramolecular oxygen‐transfer redox reaction.

Dissociation of protonated N‐(3‐phenyl‐2H‐chromen‐2‐ylidene)‐ benzenesulfonamide in the gas phase: cyclization via sulfonyl cation transfer

“…[26][27][28] An intramolecular Nto C-sulfonyl migration have also been reported in the condensed phase. [16,19] Analogously, migration of the tosyl cation and reduction of the tosyl group have been previously reported in the gas-phase fragmentation of protonated p-toluenesulfonamides. [14,15] Thus, the potential pathways for fragmentation of [1 + H] + are rationalized in Scheme 2, and the elemental compositions of these proposed product ions have been confirmed by accurate mass measurements carried out on the high-resolution QTOF mass spectrometer ( Supplementary Table S1, see Supporting Information).…”

“…Intramolecular sulfonyl migration has also been reported to occur effectively in the condensed phase, and it has received intense interest in organic synthesis, due to the high regioselectivity of the sulfonylation and the viewpoint of atom economy. [16][17][18][19] Interestingly, some of these processes involve the Nto C-sulfonyl transfer. [16,19] To the best our knowledge, however, no report has been found on the gas-phase Nto C-sulfonyl transfer, which deserves further investigation.…”