80447-93-4Relevant academic research and scientific papers
Oxidation of 1,1-disubstituted hydrazines with benzeneseleninic acid and selenium dioxide. Facile preparation of tetrazenes
Back, Thomas G.,Kerr, Russell G.
, p. 2711 - 2718 (2007/10/02)
Various 1,1-disubstituted hydrazines were oxidized with benzeneseleninic acid in methanol, generally producing the corresponding tetrazenes in high yield.Studies of the by-products of the reaction, of the effects of protic vs. aprotic solvents, and trapping experiments suggest that N-aminonitrenes are unlikely intermediates in this oxidation.An alternative mechanism involving a Pummerer-like reaction of seleninamides derived from the hydrazines is proposed.Tetrazene formation fails when the hydrazine precursor contains an aryl or p-toluenesulfonyl substiuent, or when it is highly hindered.Selenium dioxide may be employed as the oxidant instead of the seleninic acid, but is generally less efficacious in achieving high tetrazene yields.
Direct Selenation of Electron-Rich Aromatic Compounds with (Phenylseleno)dimethylsulfonium Tetrafluoroborate
Gassman, Paul G.,Miura, Asako,Miura, Takashi
, p. 951 - 954 (2007/10/02)
(Phenylseleno)dimethylsulfonium tetrafluoroborate was found to be a highly reactive selenating agent for electron-rich aromatic compounds such as aromatic amines, phenols, and aromatic ethers.Reaction took place readily at 0-25 deg C to give ca. 50percent yields of substitution para to the activating substituent.In general, anilines gave better yields then anisoles or phenols.
