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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.
To a stirred solution of p-(3-hydroxypropyl)phenol (152 mg, 1 mmol) and pyridine (0.3 mL) in acetonitrile (10 mL) at 0° was added a solution of IBTA (430 mg, 1 mmol) in acetonitrile (2 mL). The mixture was stirred at room temperature for 10 minutes, diluted with water, and extracted with diethyl ether (3 × 10 mL).
For example, (C 6 H 5)(CH 3) 2 C + is referred to as a "benzylic" carbocation. The benzyl free radical has the formula C 6 H 5 CH 2 •. The benzyl cation or phenylcarbenium ion is the carbocation with formula C 6 H 5 CH + 2; the benzyl anion or phenylmethanide ion is the carbanion with the formula C 6 H 5 CH − 2.
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Completing the cyclooctane ring required 3 more carbon atoms that were supplied by a C2 fragment in an aldol addition and a Grignard C1 fragment (scheme 2).A Mukaiyama aldol addition (magnesium bromide / toluene) took place between aldehyde 7 and ketene silyl acetal 8 with 71% stereoselectivity to alcohol 9 which was protected as the TBS ether 10 (TBSOTf, 2,6-lutidine).
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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.