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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.
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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] The mechanism involves silylation of the carbonyl oxygen and elimination of tert -butyl iodide ( 1 ), methanolysis of the silyl ester to the carbamic acid ...
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This might involve using the triflate or the less reactive chloride of TBDPS along with a mild base such as 2,6-lutidine or pyridine and potentially a catalyst such as DMAP or imidazole. [ 3 ] The ease of installation of the protecting group follows the order: 1 o > 2 o > 3 o , allowing the least hindered hydroxyl group to be protected in the ...
Trichloroethyl chloroformate is used in organic synthesis for the introduction of the trichloroethyl chloroformate (Troc) protecting group for amines, thiols and alcohols.It readily cleaves vs other carbamates and can be used in an overall protecting group strategy.
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.