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2-(2-Azidoethyl)cycloalkanones afford bridged lactams in the Aubé-Schmidt reaction, sometimes in excellent yield, and solvolysis yields derivatives of medium-ring amines. Attempts to divert the Schmidt reaction with an arene-mediated fragmentation of the normal Schmidt intermediate have led to an initial example.
- bridged amide
- medium-ring amine
- medium-ring amide
Macleod, F., Lang, S., & Murphy, J. A. (2010). The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aubé-Schmidt reaction. Synlett, 2010(4), 529-534. https://doi.org/10.1055/s-0029-1219340