Chemical and microsomal oxidation of tertiary amides: regio-and stereoselective aspects

J Iley, R Tolando

Index: Iley, Jim; Tolando, Roberto; Constantino, Luis Journal of the Chemical Society. Perkin Transactions 2, 2001 , # 8 p. 1299 - 1305

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Citation Number: 14

Abstract

The conformationally restricted tertiary amides N-methyl-2-pyrrolidone 6, N-methyl-2- piperidone 7 and N-methyl-ε-caprolactam 8 were oxidised by 5, 10, 15, 20- tetraphenylporphyrinatoiron (III) chloride/tert-butyl hydroperoxide (TPPFe/ButOOH) and by phenobarbital-induced rat liver microsomes. The products were the N-demethylated lactams together with the analogous N-methylimides and norimides. For the TPPFe/ButOOH ...