Oxidations of Amines, Amides, Ethers, Sulfides, Phosphines, Arsines, Stibines and Miscellaneous Substrates

Abstract

This chapter principally concerns oxidations of organic substrates containing N, O, S, P, As and Sb. Oxidations of amines are covered first, including primary amines to nitriles or amides; secondary amines to imines or other products; tertiary amines to N-oxides or other products (Section 5.1) and the oxidation of amides (5.2). Oxidation of ethers to esters or lactones follows (5.3), then of sulfides to sulfoxides or sulfones (5.4) and of phosphines, arsine and stibines to their oxides (5.5). A final section (5.6) concerns such miscellaneous oxidations not covered by other sections in the book. Oxidation of AminesThe subject of Ru-catalysed amine oxidations has been reviewed [1][2][3][4][5][6][7]. The first catalytic oxidation (1978) used RuCl 3 /O 2 /water-toluene/100°C 1 to oxidise primary and secondary amines to nitriles and imines respectively [8].Some oxidations of primary and secondary amines (and of amides) may be considered as amine or as alkane oxidations (in this latter instance as of CH, CH 2 or CH 3 groups): for convenience they are dealt with here as amine oxidations, but cross-references with Chapter 4 are given where appropriate; cf. 4.1.2, 4.1.3 and 5.1.3.1. Primary