60423-73-6Relevant academic research and scientific papers
STUDY OF THE HYDROXYLATION OF N-SUBSTITUTED 1,2,5,6-TETRAHYDROPYRIDINES
Maksimova, T. N.,Mochalin, V. B.,Unkovskii, B. V.
, p. 604 - 607 (1980)
N-Substituted 1,2,5,6-tetrahydropyridines are readily converted to the corresponding 1,2-diols by treatment with an aqueous solution of potassium permanganate in a neutral medium.The yields of the desired products depend on the character of the substituent attached to the nitrogen atom and decrease in the case of N-methyl-1,2,5,6-tetrahydropyridines as a consequence of the formation of side products formed as a result of more profound oxidation.The acylation of the synthesized diols was studied.The three-dimensional structures of the synthesized cis-diols were established by IR spectroscopy.
Osmium-Catalyzed Dihydroxylation of Olefins in Acidic Media: Old Process, New Tricks
Dupau, Philippe,Epple, Robert,Thomas, Allen A.,Fokin, Valery V.,Sharpless, K. Barry
, p. 421 - 433 (2007/10/03)
A screen of over 500 diversely functionalized additives in osmium-catalyzed dihydroxylation has uncovered that electron-deficient olefins are converted into the corresponding diols much more efficiently when the pH of the reaction medium is maintained on the acidic side. Further studies have identified citric acid as the additive of choice, for it allows preparation of very pure diols in yields generally exceeding 90%. As described here, a much wider range of olefin classes can now be successfully dihydroxylated. The process is experimentally simple, in most cases involving little more than dissolving the reactants in water or a waler/tertbutyl alcohol mixture, stirring them, and filtering off the pure diol product.
