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Osazone formation was developed by Emil Fischer, [3] who used the reaction as a test to identify monosaccharides. The formation of a pair of hydrazone functionalities involves both oxidation and condensation reactions. [4] Since the reaction requires a free carbonyl group, only "reducing sugars" participate.
The Sharpless asymmetric dihydroxylation [7] was developed by K. Barry Sharpless to use catalytic amounts of OsO 4 along with the stoichiometric oxidant K 3 [Fe(CN) 6]. [1] [2] [8] The reaction is performed in the presence of a chiral auxiliary. The selection of dihydroquinidine (DHQD) or dihydroquinine (DHQ) as a chiral auxiliary dictates the ...
The reagent was originally generated in situ by reducing iron pentacarbonyl with sodium amalgam. [5] Modern synthesis use sodium naphthalene or sodium benzophenone ketyls as the reducants: [1] [6] Fe(CO) 5 + 2 Na → Na 2 [Fe(CO) 4] + CO. When a deficiency of sodium is used, the reduction affords deep yellow octacarbonyl diferrate: [1]
The trimethyloxonium salt is available from dimethyl ether via an analogous route. [6] These salts do not have long shelf-lives at room temperature. They degrade by hydrolysis: [Et 3 O] + [BF 4] − + H 2 O → Et 2 O + EtOH + H + [BF 4] −. The propensity of trialkyloxonium salts for alkyl-exchange can be advantageous.
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The photochemical rearrangement of the obtained 1-N-iminipyridinium ylides leads in high yields to 1H-1,2-diazepines [14] Synthesis of 1,2-Diazepinen aus Iminopyridiniumyliden N -amination of 1 H -benzotriazole with hydroxylamine- O -sulfonic acid yields a mixture of 1-aminobenzotriazole (major product) and 2-aminobenzotriazole (minor product).
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