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Lead(IV) acetate or lead tetraacetate is an metalorganic compound with chemical formula Pb(C 2 H 3 O 2) 4. It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis. [2]
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. This oxidation was discovered by Rudolf Criegee and coworkers and first reported in 1931 using ethylene glycol as ...
The reason is that with inorganic lead compounds elements such as nitrogen, oxygen and the halides have a much higher electronegativity than lead itself and the partial positive charge on lead then leads to a stronger contraction of the 6s orbital than the 6p orbital making the 6s orbital inert; this is called the inert-pair effect.
The unusual alkyl nitrite starting material of the Barton reaction is prepared by attack of an alcohol on a nitrosylium cation generated in situ by dehydration of doubly protonated nitrous acid. [6] This series of steps is mechanistically identical to the first half of the mechanism formation of the more well-known aryl and alkyl diazonium salts.
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.
Glycol cleavage is a specific type of organic chemistry oxidation. 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]
Other methods for the α-hydroxylation of carbonyl compounds may employ toxic organometallic compounds (such as lead tetraacetate or osmium tetroxide). One alternative to hypervalent iodine oxidation that does not employ heavy metals is the attack of a metal enolate on dioxygen, followed by reduction of the resulting peroxide (equation ( 14 )).
Lead(II) oxide is also soluble in alkali hydroxide solutions to form the corresponding plumbite salt. [2] PbO + 2 OH − + H 2 O → Pb(OH) 2− 4. Chlorination of plumbite solutions causes the formation of lead's +4 oxidation state. Pb(OH) 2− 4 + Cl 2 → PbO 2 + 2 Cl − + 2 H 2 O. Lead dioxide is representative of the +4 oxidation state ...