Tetrahedron Letters p. 4207 - 4210 (1989)
Update date:2022-08-15
Topics:
Hoffman, Robert V.
Salvador, James M.
A new method is reported for the direct preparation of N-substituted lactams from cycloalkanones.N-(p-nitrobenzenesulfonoxyl) methylamine 1a (CH3NH-OSO2C6H4NO2) was reacted with a series of cycloalkanones to give good yields of N-methyl lactams.An addition-rearrangement pathway accounts for the ring-expanded lactam products.A series of N-alkyl-N-arylsulfonoxyl amines were generated in situ and reacted with cyclobutanone to give N-alkyl pyrrolidinones in high yields.
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