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The carbon–carbon bond in a vicinal diol (glycol) is cleaved and instead the two oxygen atoms become double-bonded to their respective carbon atoms. Depending on the substitution pattern in the diol, these carbonyls will be ketones and/or aldehydes. [1] Glycol cleavage is an important for determining the structures of sugars.
Through a variety of mechanisms, the removal of a hydride equivalent converts a primary or secondary alcohol to an aldehyde or ketone, respectively. The oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (gem-diol, R-CH(OH) 2) by reaction with water ...
Two mechanisms are proposed for the Criegee oxidation, depending on the configuration of the diol. [6] [7] If the oxygen atoms of the two hydroxy groups are conformationally close enough to form a five-membered ring with the lead atom, the reaction occurs via a cyclic intermediate.
Periodic acid (/ ˌ p ɜːr aɪ ˈ ɒ d ɪ k / per-eye-OD-ik) is the highest oxoacid of iodine, in which the iodine exists in oxidation state +7. It can exist in two forms: orthoperiodic acid, with the chemical formula H 5 IO 6 , and metaperiodic acid, which has the formula HIO 4 .
LiBr reacts with NaIO 4 and acetic acid to produce lithium acetate, which can then proceed through the reaction as previously mentioned. The protocol produced high dr for the corresponding diol, depending on the oxidant chosen. The modification of the Prevost-Woodward reaction proposed by Sudalai.
Two ketyl groups react in a coupling reaction yielding a vicinal diol with both hydroxyl groups deprotonated. Addition of water or another proton donor gives the diol. With magnesium as an electron donor, the initial reaction product is a 5-membered cyclic compound with the two oxygen atoms coordinated to the oxidized Mg 2+ ion.
An α,β-epoxyketone reacts with hydrazine hydrate to yield an allylic alcohol. [7] In the synthesis of warburganal, a bioactive natural product, the α,β-epoxyketone is formed from a cyclic α,β-unsaturated ketone and in a separate step reacts under the classical Wharton olefin synthesis conditions to yield an allylic diol. [8]
A different monomer with two identical functional groups, such as a dioyl dichloride or dioic acid is required to continue the process of polymerization through repeated esterification processes. A diol can be converted to cyclic ether by using an acid catalyst, this is diol cyclization. Firstly, it involves protonation of the hydroxyl group.