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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]
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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.
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.
R = heteroatom, alkyl, aryl, allyl etc. or other substituents. In organic chemistry , benzyl is the substituent or molecular fragment possessing the structure R−CH 2 −C 6 H 5 . Benzyl features a benzene ring ( C 6 H 6 ) attached to a methylene group ( −CH 2 − ).
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.
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 ...
Trimethylsilyl trifluoromethanesulfonate has a variety of other specialized uses. It has been used to install tert-alkyl groups on phosphine (R = alkyl): [6] PH 3 + R 3 C–OAc + Me 3 SiOTf → [(R 3 C) 2 PH 2]OTf. Deprotection of Boc-protected amines can be achieved using trimethylsilyl trifluoromethanesulfonate and triethylamine or 2,6 ...