Search results
Results from the WOW.Com Content Network
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
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. Periodic acid was discovered by Heinrich Gustav Magnus and C. F ...
Acid 19 was converted to lactone 20 (acetic anhydride, sodium acetate) and reaction with methylmagnesium chloride gave tetracyclic ketone 21. Treatment with periodic acid (dioxane) and piperidine acetate (benzene) gave aldehyde 24 through diol 22 (oxidation) and dialdehyde 23 (aldol condensation).
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.
The chemical reaction called Sharpless asymmetric dihydroxylation can be used to produce chiral diols from alkenes using an osmate reagent and a chiral catalyst. Another method is the Woodward cis-hydroxylation (cis diol) and the related Prévost reaction (anti diol), which both use iodine and the silver salt of a carboxylic acid.
The Criegee oxidation is a glycol cleavage reaction in which vicinal diols are oxidized to form ketones and aldehydes using lead tetraacetate.It is analogous to the use of periodate (Malaprade reaction) but uses a milder oxidant.
Dess–Martin periodinane (DMP) is a chemical reagent used in the Dess–Martin oxidation, oxidizing primary alcohols to aldehydes and secondary alcohols to ketones. [1] [2] This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions (room temperature, neutral pH), shorter reaction times, higher yields, simplified workups, high chemoselectivity ...