Some reactions of 2,4,4-trimethyl-1-pyrroline 1-oxide

Rearrangement of N-Oxyenamines and Related Reactions

“…4-Substituted pyrroline N -oxides 368 (R 3 = Me, Ph, R 2 = H) gave mostly high diastereoselectivity, e.g., sole formation of the 3,4- cis -isomer . With an excess of reagent the rearrangement product also underwent acylation to give the enamide 373 . Under more harsh conditions the ketone 374 was isolated (Scheme ) …”

C−H Reactivity of the α‐Position in Nitrones and Nitronates

“…The most straightforward way to generate N ‐oxyenamines of type 133 is the direct acylation of nitrones/nitronates (Scheme ). In the literature, numerous examples of the synthesis of α‐acyloxy‐substituted imines by nitrone acylation have been reported (for early reports by Todd and Barton on the acylation/[3,3]‐sigmatropic rearrangement of nitrones, see).…”