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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]
Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure. For example, the amino acid tyrosine could be protected as a benzyl ester on the carboxyl group, a fluorenylmethylenoxy carbamate on the amine group, and a tert-butyl ether on the phenol
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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 .
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.
Figure 1. Cartoon representation (left) and a concrete example of a third generation dendronized polymer (right). The peripheral amine groups are modified by a substituent X which often is a protection group. Upon deprotection and modification substantial property changes can be achieved. The subscript n denotes the number of repeat units.
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).