T. Rosenau, A. Potthast, H. Sixta
Apr 8, 2002
Citations
1
Influential Citations
15
Citations
Journal
Tetrahedron
Abstract
Abstract The two carbon-centered radicals 4-morpholinomethyl ( 4 ) and 4-methylmorpholin-3-yl ( 5 ), generated from the primary cation radical intermediate 3 by β-deprotonation, are the major radical species in reaction mixtures of N -methylmorpholine- N -oxide ( 1 ) as demonstrated by trapping reactions with γ-tocopherol. Carbon–carbon coupling products originating from the recombination of 4 and the reaction between 4 and 5 have been identified. Recombination of 4 with the primary cation radical 3 was shown to be the key step in the ‘disproportionation’ of 3 into N -methylmorpholine, morpholine and formaldehyde.