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Chlorierung der Alkoxyamine (I) mit tBuOCl liefert die N‐Chlor‐N‐alkoxyamine (II), die mit den Alkoholen (III) in Gegenwart von Et3N als Base [zur Synthese von (IVa) wird Na‐methylat als Base verwendet] unter nucleophiler Substitution zu den N,N‐Dialkoxyaminen (IV) reagieren; neben (IVd) bzw. (IVf) entstehen die Azoxy‐Verbindungen (Va) ( 12% Ausb.) bzw. (Vb) ( 26%).

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Electrophilically catalysed cleavage of the N-0 bond of N,N-dimethoxyamine results in the formation o f singlet N-methoxynitrenium ion, which aminates soft nucleophiles, methylates hard ones, and epiminates alkenes.Two electronegative N-substituents in N,N-dialkoxyamines' amines and N-alkoxyamines. However, N,N-dialkoxyamines significantly decrease the p character of the nitrogen lone undergo reactions typical for ~~o n d a r y amines; hydroxy-and electron pair. Therefore, these compounds are characterized amino-methylation,' acylation and carbamoylation,2 and by a higher pyramidal stability [AGfn,, -20 kcal mol-1(1 cal = N-~hlorination.~ They are also easily oxidised forming stable 4.184 J)]' and weaker nucleophilicity 1 compared to common N,N-dialkoxyaminYl radicals.4

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