Synthesis of alpha,beta-unsaturated ketones as chalcone analogues via a S(RN)1 mechanism

Synthesis of alpha,beta-unsaturated ketones as chalcone analogues via a S(RN)1 mechanism

An electron-transfer chain reaction between 2-nitropropane anion and alpha-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-yl)ethanone or 2-bromo-1-(4-nitrophenyl)ethanone...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2007-04, Vol.12 (4), p.797-804
Hauptverfasser: Curti, Christophe, Gellis, Armand, Vanelle, Patrice
Format: Artikel
Sprache:eng
Schlagworte:
Anions - chemistry
Chalcone - analogs & derivatives
Chemistry - methods
Electrons
Ketones - chemical synthesis
Ketones - chemistry
Magnetic Resonance Spectroscopy
Models, Chemical
Molecular Conformation
Molecular Structure
Propane - chemistry
Quaternary Ammonium Compounds - chemistry
Solvents - chemistry
Temperature
Thiophenes - chemistry
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Beschreibung
Zusammenfassung:An electron-transfer chain reaction between 2-nitropropane anion and alpha-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-yl)ethanone or 2-bromo-1-(4-nitrophenyl)ethanone were reacted with several cyclic nitronate anions to form alpha,beta-unsaturated ketones via a S(RN)1 mechanism. This new method can be used to synthesize a wide variety of chalcone analogues.
ISSN:1420-3049
DOI:10.3390/12040797