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Phenylhydrazine was the first hydrazine derivative characterized, reported by Hermann Emil Fischer in 1875. [7] [8] He prepared it by reduction of a phenyl diazonium salt using sulfite salts. Fischer used phenylhydrazine to characterize sugars via formation of hydrazones known as osazones with the sugar aldehyde. He also demonstrated in this ...
Phenylhydrazine and 2,4-dinitrophenylhydrazine had been used historically in analytical chemistry to detect and identify compounds with carbonyl groups. Phenylhydrazine was used to study the structure of carbohydrates, because the reaction of the sugar's aldehyde groups lead to well crystallizing phenylhydrazones or osazones.
Hydrazine, organohydrazines, and 1,1-diorganohydrazines react with aldehydes and ketones to give hydrazones. Phenylhydrazine reacts with reducing sugars to form hydrazones known as osazones, which was developed by German chemist Emil Fischer as a test to differentiate monosaccharides. [4] [5]
The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions. [1] [2] The reaction was discovered in 1883 by Emil Fischer. Today antimigraine drugs of the triptan class are often synthesized by this method. The Fischer ...
Since the reaction requires a free carbonyl group, only "reducing sugars" participate. Sucrose, which is nonreducing, does not form an osazone. A typical reaction showing the formation of an osazone. D-glucose reacts with phenylhydrazine to give glucosazone. The same product is obtained from fructose and mannose.
Unmixed hydrazine was referred to as B-Stoff by the Germans, a designation also used later for the ethanol/water fuel for the V-2 missile. [25] Hydrazine is used as a low-power monopropellant for the maneuvering (RCS/Reaction control system) thrusters of spacecraft, and was used to power the Space Shuttle's auxiliary power units (APUs). In ...
This reaction is, overall, a condensation reaction as two molecules joining together with loss of water. Mechanistically, it is an example of addition-elimination reaction: nucleophilic addition of the -NH 2 group to the C=O carbonyl group, followed by the elimination of a H 2 O molecule: [3] X-ray structure of DNP-derived hydrazone of ...
The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. [1] [2] In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step.