Oxidative cleavage of lactams in water using dioxiranes: an expedient and environmentally-safe route to ω-nitro acids

C Annese, L D'Accolti, R Filardi, I Tommasi, C Fusco

Index: Annese, Cosimo; D'Accolti, Lucia; Filardi, Rosella; Tommasi, Immacolata; Fusco, Caterina Tetrahedron Letters, 2013 , vol. 54, # 6 p. 515 - 517

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Citation Number: 4

Abstract

By taking advantage of the appreciable stability of dioxiranes in water, a safe yet efficient route to ω-nitro acids by oxidation of lactams of various ring sizes under mild conditions has been reported. In essentially all the cases examined, reactions proceed selectively to afford products in remarkably high yields (up to 99%) and with high purity (94–99%). Also, an interesting example of higher reaction selectivity in water than in organic solvent ( ...