Tetrahedron

Selectivities in the oxidation of tertiary amines and pyridine derivatives by perfluoro cis-2, 3-dialkyloxaziridines

A Arnone, P Metrangolo, B Novo, G Resnati

Index: Arnone, Alberto; Metrangolo, Pierangelo; Novo, Barbara; Resnati, Giuseppe Tetrahedron, 1998 , vol. 54, # 27 p. 7831 - 7842

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Citation Number: 15

Abstract

When tertiary amines 1 are reacted with perfluoro cis-2, 3-dialkyloxaziridines 2 at− 60° C corresponding N-oxides 3 are formed in high yields. The process is chemoselective and diastereoselective. The chemoselectivity in the reaction of alkenyl substituted pyridines is solvent dependent, attack occurring exclusively at the carbon-carbon double bond or at the nitrogen atom under protic and aprotic conditions, respectively. Lower selectivities were ...