122901-86-4Relevant articles and documents
Der Einfluss struktureller Faktoren auf die Dimerisierung von Vinylnitroxiden mit cyclischen Acylgruppen als β-Substituenten
Aurich, Hans Guenter,Franzke, Michael,Kesselheim, Hans-Peter,Kessler, Wilfried,Massa, Werner,Wocadlo, Sigrid
, p. 513 - 521 (2007/10/02)
Nitroxides (Aminyl Oxides), 43.- The Effect of Structural Features upon the Dimerization of Vinyl Nitroxides Substituted in β-Position by cyclic Acyl Groups Reaction between N-alkyl- and N-arylhydroxylamines and hydroxymethylene compounds 4 (derivatives of menthone, norbornanone, bornanone, indanone, and γ-butyrolactone) affords nitrones existing in the tautomeric forms 5 and 6.Oxidation of these nitrones generates the β-acylated vinyl nitroxides 7, which dimerize in various ways.The N-alkyl-susbstituted vinyl nitroxides 7Da, De, Ea, Ga, and Gf yield simple CC-bonded dimers 8.From 7Ba dimer 10 is formed via 8Ba.The structure of 10 is confirmed by an X-ray analysis.In contrast, the N-aryl-substituted vinyl nitroxides 7Ab, Fc, and Bc as well as the N-alkyl-substituted 7Aa afford the bicyclic dimers 9 which arise by OC dimerization followed by an intramolecular 1,3-dipolar cycloaddition.Finally, the vinyl nitroxides 7Dc and Dd underwent further oxidation to give dehydrodimers 12. 12e is formed only if 6De is oxidized by a large excess of lead dioxide.
