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The general features of this synthesis are: 1) the epoxidation of α,β-unsaturated ketones is achieved usually in basic conditions using hydrogen peroxide solution in high yield; 2) the epoxy ketone is treated with 2–3 equivalents of a hydrazine hydrate in presence of substoichiometric amounts of acetic acid. This reaction occurs rapidly at ...
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.
The Albright–Goldman oxidation is a name reaction of organic chemistry, first described by the American chemists J. Donald Albright and Leon Goldman in 1965. [1] The reaction is particularly suitable for the synthesis of aldehydes from primary alcohols. Analogously, secondary alcohols can be oxidized to form ketones.
When derived from hydrazine itself, hydrazones condense with a second equivalent of a carbonyl to give azines: [11] R 2 C=N−NH 2 + R 2 C=O → R 2 C=N−N=CR 2 + H 2 O. Hydrazones are intermediates in the Wolff–Kishner reduction. Hydrazones are reactants in hydrazone iodination, the Shapiro reaction, and the Bamford–Stevens reaction to ...
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 ...
The Vilsmeier–Haack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted formamide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5): RC(=O)NR ′ R″ + HArZ + POCl 3 + H 2 O → RC(=O)ArZ + NR ′ R″H + HCl + H 3 PO 4
The mechanism of the McFadyen–Stevens reaction is still under investigation. Two groups have independently proposed a heterolytic fragmentation mechanism. [4] [5] The mechanism involves the deprotonation of the acyl sulfonamide followed by a 1,2-hydride migration to give the alkoxide ( 3 ).
[8] [9] [10] Upon workup by acidic hydrolysis the primary amine is liberated as the amine salt. [11] Alternatively the workup may be via the Ing–Manske procedure, involving reaction with hydrazine. This method produces a precipitate of phthalhydrazide (C 6 H 4 (CO) 2 N 2 H 2) along with the primary amine: C 6 H 4 (CO) 2 NR + N 2 H 4 → C 6 H ...