81003-51-2Relevant articles and documents
Reactions with Nitrosodisulfonate, 40. Oxidation of Keto-Enols
Teuber, Hans-Joachim,Hohn, Juergen
, p. 90 - 98 (2007/10/02)
Potassium nitrosodisulfonate oxidizes dihydroresorcinol and dimedone to give the corresponding 1,2,3-cyclohexanetriones.These are transformed by aldol reaction with the starting ketones into 1 and 2a, respectively.Oxindole analogously yields 3. 1 and 2a suffer retraldol fission by phenylhydrazine and hydroxylamine forming the derivatives of the vicinal triketones (4, 5).Acetic anhydride, sulfuric acid, and HBr/acetic acid render the ketol ring fully aromatic (6, 7a, b) and close a furan ring (7a, b).Additionally, the symmetric tetrahydro-tetrahydroxy-biphenyl 9 is formed. - The reaction path way is discussed.