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Pigment Yellow 97, a popular yellow colorant, is a hydrazone. [6]Hydrazones are the basis for various analyses of ketones and aldehydes. For example, dinitrophenylhydrazine coated onto a silica sorbent is the basis of an adsorption cartridge.
Benzophenone is a naturally occurring organic compound with the formula (C 6 H 5) 2 CO, generally abbreviated Ph 2 CO. Benzophenone has been found in some fungi, fruits and plants, including grapes. [4] It is a white solid with a low melting point and rose-like odor [5] that is soluble in organic solvents. Benzophenone is the simplest ...
X-ray structure of DNP-derived hydrazone of benzophenone. Selected parameters: C=N, 128 pm; N-N, 1.38 pm, N-N-C(Ar), 119 [4] When 3-heptanone is added to a solution of 2,4-DNPH and heated, an orange-red precipitate forms. DNP-derived hydrazones have characteristic melting points, facilitating identification of the carbonyl.
The hydrazone products of the Japp–Klingemann reaction are most often used as intermediates in syntheses of more complex organic molecules. For example, a phenylhydrazone product can be heated in the presence of strong acid to produce an indole via the Fischer indole synthesis .
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.
Many ketones contain the benzoyl group. They have the formula C 6 H 5 CO–R, an important example being benzophenone. Benzoyl esters and amides are common in organic chemistry. The esters are used as a protecting groups in organic synthesis, [4] which can be easily removed by hydrolysis in dilute basic solution.
[3] [4] An example of a transition metal-catalyzed cyclopropanation is a synthesis of tranylcypromine, [5] [6] in which the sodium salt of benzaldehyde tosylhydrazone is converted to a rhodium metal carbene through the diazo intermediate. Tosylhydrazones are also starting materials for certain cross-coupling reactions. [7]
Two equivalents of strong base such as n-butyllithium abstract the proton from the hydrazone (4) followed by the less acidic proton α to the hydrazone carbon (5), forming a carbanion. The carbanion then undergoes. an elimination reaction producing a carbon–carbon double bond and ejecting the tosyl anion, forming a diazonium anion (6).