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Reactions of Trialkylsilyl Trifluoromethanesulfonates, VIII. – Synthesis of O-(Trimethylsilyl)ketene O,N-Acetals, 2,5-Bis(trimethylsiloxy)pyrroles, -furans, and -thiophenes
Ketene O,N-acetals 3, 4, 6, 8 are obtained from N,N-diarylcarboxamides and N-acetylheterocycles 5, 7 by silylation with trimethylsilyl triflate (2) in the presence of triethylamine.Analogous reactions of carboxamides 9 and N-acyllactams 11 yield the ketene O,N-acetals 10, 12.Succinimides 13, succinic anhydrides 20, and succinic thioanhydrides 22 are doubly silylated by 2 to give the 2,5-bis(trimethylsiloxy)heterocycles 14, 21, 23. 2,5-Bis(trimethylsiloxy)furan (21a) reacts with aldehyde acetals and orthoesters 24 catalyzed by 2 to yield 2,3-disubstituted succinic anhydrides 25.
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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem