ANODIC OXIDATION OF DIARYLACETYLENES AND DIARYLDIACETYLENES: ELECTROSYNTHESIS OF DIAROYL-STILBENES AND ACETYLENIC α- AND γ-DIKETONES
Diarylacetylenes and diaryldiacetylenes have been electrooxidized in acetonitrile through the use of a graphite plate anode, thus overcoming a very high passivation.Diarylacetylenes led mainly to 1,2-diaroyl-1,2-diaryl-ethylenes.Anodic oxidation of conjugated diaryldiacetylenes, at the same anode, led to a mixture of acetylenic α- and γ-diketones.This represents the very first synthesis of acetylenic α-diketones Ar-CO-CO-CC-Ar.
Reaction of Azibenzils with Nonofluorobutanesulfonic Anhydride
Reaction of azibenzils 1a - e with nonafluorosulfonebutanesulfonic anhydride (Nf2O) yields mainly vinylene bis(nonofluorobutanesulfonates) E,Z-2a - e and benzils 3a - e.The presence of a non-nucleophilic amine prevents decomposition of the azibenzils by traces of acid in the anhydride.Compounds 2 stem from an initial O-sulfonylation of the azibenzils, whereas C-sulfonylation perhaps leads to the benzils.Diazodiphenylmethane is decomposed by Nf2O to give tetraphenylethylene, benzophenone, and benzophenone azine.
Lorenz, Wolfgang,Maas, Gerhard
p. 2220 - 2232
(2007/10/02)
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