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Protecting Group Sensitivity to Jones Oxidation

Although Jones oxidation is carried out in the presence of aqueous sulfuric acid, functionalities with a high sensitivity to acidic conditions can remain unchanged due to the segregation between the organic and aqueous phases. [Pg.8]

Only very acid-sensitive protecting groups are hydrolyzed under the conditions of the Jones oxidation. When free alcohols result from the hydrolysis of very acid-sensitive protecting groups, they are in situ oxidized to ketones or carboxylic acids. [Pg.8]

It must be mentioned that diverse acid strengths, temperatures and reaction times are used in Jones oxidation, which leads to uneven responses of the same protecting groups. [Pg.8]

Most silyl ethers, including the ubiquitous TBS ethers,22 resist Jones oxidation, with the exception of the very acid-sensitive TMS ethers.23 [Pg.8]

Anomalous cases are known in which the normally robust TBS ethers are hydrolyzed.24 Contrastingly, rare instances have been published in which the sensitive TMS ethers remain unchanged25 under Jones oxdation. [Pg.8]


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Group oxides

Jones oxidation

Jones oxidation protecting group sensitivity

Oxidants Jones

Oxidation, sensitized

Oxidizing group

Protecting group sensitivity

Protective oxidation

Protective oxides

Sensitive protecting groups

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