Tertiary Amine Oxidation using HOF centre dot CH_3CN: A Novel Synthesis of N-Oxides

摘要

HOF centre dot CH_3CN, probably the best oxygen transfer agent organic chemistry has to offer, is easily made by bubbling diluted fluorine (10-15%) through aqueous acetonitrile solution. Used as formed without any isolation or purification, it reacts with various tertiary amines such as pyridine derivatives, polyaromatic nitrogen containing compounds and aliphatic and alicyclic ones to form the corresponding N-oxides. When two nitrogen atoms are present it is possible to make both the N-monoxides and the N, N-dioxides. The reaction times are short (a few minutes), conditions are very mild (0-25 deg C) and the yields range from good to excellent (70-95%).