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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (or DDQ) is the chemical reagent with formula C 6 Cl 2 (CN) 2 O 2. This oxidant is useful for the dehydrogenation of alcohols, [3] phenols, [4] and steroid ketones. [5] DDQ decomposes in water, but is stable in aqueous mineral acid. [6]
The use of protective groups is pervasive but not without criticism. [103] In practical terms their use adds two steps (protection-deprotection sequence) to a synthesis, either or both of which can dramatically lower chemical yield. Crucially, added complexity impedes the use of synthetic total synthesis in drug discovery.
p-Methoxybenzyl (PMB) is used as a protecting group for alcohols in organic synthesis (4-Methoxybenzylthiol is used to protect thiols). The p -methoxybenzyl group Strong base such as powdered potassium hydroxide or sodium hydride and p -methoxybenzyl halide (chloride or bromide) [ 14 ] [ 15 ]
It is also a good test for the successful deprotection of a secondary amine. Secondary amines react with chloranil to give a brown/red/orange derivative, the colour depending on the amine. In these reactions, the amine displaces chloride from the ring of the quinone.
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[5] [6] Selective cleavage of the N-Boc group in the presence of other protecting groups is possible when using AlCl 3. Sequential treatment with trimethylsilyl iodide then methanol can also be used for Boc deprotection, [7] [8] especially where other deprotection methods are too harsh for the substrate. [9]
Benzyl chloroformate is commonly used in organic synthesis for the introduction of the benzyloxycarbonyl (formerly called carboxybenzyl) protecting group for amines.The protecting group is abbreviated Cbz or Z (in honor of discoverer Zervas), hence the alternative shorthand designation for benzyl chloroformate as Cbz-Cl or Z-Cl.