Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones.
نویسندگان
چکیده
2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro-1-arylethen-1-olates and trapped with a range of electrophiles resulting in either reduction, reduction/aldol, reduction/Claisen condensation or reduction/aldol-Tishchenko products. In addition we demonstrate that 2,2-dichloro-1-arylethen-1-olates undergo counter-ion controlled Darzens condensations, which can be followed by a thermal rearrangement as a route to 1,3-diaryl-3-chloropropane-1,2-diones.
منابع مشابه
Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: mechanistic investigation and the synthesis of substituted α,α-dichloroketones.
2,2,2-Trichloro-1-arylethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-arylethanones in the presence of RMgX. A single electron transfer mechanism for the reaction is proposed based on trapping experiments. Reaction of the intermediate enolates with a range of electrophiles is described, providing a convenient route to substituted α,α-dichloro-β-hydroxyketones and ...
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2,2,2-Trichloro-1-arylethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-arylethanones in the presence of RMgX. A single electron transfer mechanism for the reaction is proposed based on trapping experiments. Reaction of the intermediate enolates with a range of electrophiles is described, providing a convenient route to substituted a,a-dichloro-b-hydroxyketones and ...
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 13 20 شماره
صفحات -
تاریخ انتشار 2015