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The mechanism of phenol oxidation with hypervalent iodine reagents begins with the formation of an aryloxyiodonium(III) intermediate. Inter- or intramolecular nucleophilic attack then takes place, either in one step or in two via an oxenium ion. [4]
4-Hydroxyacetophenone 4'-Hydroxyacetophenone p-Hydroxyacetophenone. Identifiers CAS Number. ... Anticonvulsants are also possible by Mannich reaction: [5] Metabolism
The mechanism of carbonyl oxidation by iodine(III) reagents varies as a function of substrate structure and reaction conditions, but some generalizations are possible. Under basic conditions, the active iodinating species are iodine(III) compounds in which any relatively acidic ligands on iodine (such as acetate) have been replaced by alkoxide. [1]
Here is the mechanism of this reaction: The mechanism for bromination of benzene. The mechanism for iodination is slightly different: iodine (I 2) is treated with an oxidizing agent such as nitric acid to obtain the electrophilic iodine ("I +", probably IONO 2). Other conditions for iodination include I 2, HIO 3, H 2 SO 4, and N-iodosuccinimide ...
Hydrazone iodination is an organic reaction in which a hydrazone is converted into a vinyl iodide by reaction of iodine and a non-nucleophilic base such as DBU. [1] [2] First published by Derek Barton in 1962 the reaction is sometimes referred to as the Barton reaction (although there are many different Barton reactions) or, more descriptively, as the Barton vinyl iodine procedure.
These methods work best when the iodide product is stable to hydrolysis; otherwise, the possibilities include high-temperature oxidative iodination of the element with iodine or hydrogen iodide, high-temperature iodination of a metal oxide or other halide by iodine, a volatile metal halide, carbon tetraiodide, or an organic iodide.
The iodinium ion is opened via S N 2 reaction by acetic acid (or silver acetate) to give the first intermediate, the iodo-acetate (4). Through anchimeric assistance, the iodine is displaced via another S N 2 reaction to give an oxonium ion (5), which is subsequently hydrolyzed to the give the mono-ester (6). The mechanism of the Woodward cis ...
Hydrazones can also be synthesized by the Japp–Klingemann reaction via β-keto acids or β-keto-esters and aryl diazonium salts. Hydrazones are converted to azines when used in the preparation of 3,5-disubstituted 1 H - pyrazoles , [ 12 ] a reaction also well known using hydrazine hydrate .