In organic chemistry, the Doering–LaFlamme allene synthesis is a reaction of alkenes that converts them to allenes by insertion of a carbon atom. This name reaction is named for William von Eggers Doering and a co-worker, who first reported it.
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| - Doering-LaFlamme-Allensynthese (de)
- Síntesis de alenos de Doering-LaFlamme (es)
- Doering–LaFlamme allene synthesis (en)
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| - Bei der Doering-LaFlamme-Allensynthese handelt es sich um eine Namensreaktion aus der organischen Chemie. Die Reaktion ist nach dem US-amerikanischen Chemiker W. von E. Doering und P. M. LaFlamme benannt und wurde 1958 publiziert. Sie ermöglicht die Synthese von Allenen aus Olefinen in zwei Schritten. (de)
- In organic chemistry, the Doering–LaFlamme allene synthesis is a reaction of alkenes that converts them to allenes by insertion of a carbon atom. This name reaction is named for William von Eggers Doering and a co-worker, who first reported it. (en)
- En química orgánica, la síntesis de alenos de Doering–LaFlamme es un método de síntesis de dienos acumulados (cumulenos) por inserción de un átomo de carbono. Esta reacción es nombrada en honor a los químicos William von Eggers Doering y un colaborador, quién lo reportó previamente. (es)
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| - Bei der Doering-LaFlamme-Allensynthese handelt es sich um eine Namensreaktion aus der organischen Chemie. Die Reaktion ist nach dem US-amerikanischen Chemiker W. von E. Doering und P. M. LaFlamme benannt und wurde 1958 publiziert. Sie ermöglicht die Synthese von Allenen aus Olefinen in zwei Schritten. (de)
- In organic chemistry, the Doering–LaFlamme allene synthesis is a reaction of alkenes that converts them to allenes by insertion of a carbon atom. This name reaction is named for William von Eggers Doering and a co-worker, who first reported it. The reaction is a two-stage process, in which first the alkene is reacted with dichlorocarbene or dibromocarbene to form a dihalocyclopropane. This intermediate is then reacted with a reducing metal, such as sodium or magnesium, or with an organolithium reagent. Either approach results in metal-halogen exchange to convert the gem-dihalogenated carbon to a 1-metallo-1-halocyclopropane. This species undergoes α-elimination of metal halide and ring-opening via an electrocyclic reaction (at least formally) to give the allene. Several different mechanisms for the electrocyclic rearrangement have been studied. In a study in which an enantioenriched substituted cyclopropyl Grignard reagent was prepared, the reaction was shown to give the allene with very high levels of enantiospecificity, suggesting a concerted mechanism. Similarly, in a computational study of the bromolithiocyclopropane, a concerted mechanism was found to be favored. A discrete cyclopropylidene carbene was found to be unlikely, although early ejection of LiBr (roughly simultaneous to C–C bond scission and before formation of the orthogonal pi bonds of the allene) was suggested. (en)
- En química orgánica, la síntesis de alenos de Doering–LaFlamme es un método de síntesis de dienos acumulados (cumulenos) por inserción de un átomo de carbono. Esta reacción es nombrada en honor a los químicos William von Eggers Doering y un colaborador, quién lo reportó previamente. El método de síntesis consta de dos etapas: en la primera se hace reaccionar un alqueno con un diclorocarbeno o dibromocarbeno para formar un dihalociclopropano. En la segunda etapa, se hace reaccionar a este intermediario con un metal reductor, como sodio o magnesio, o con un reactivo de organolitio. Cualquiera de los dos métodos convierte el carbono dihalogenado en una estructura carbenoide o similar a carbenoide. El ciclopropilcarbeno resultante se transpone para formar el aleno como producto . La naturaleza electrónica del carbeno intermedio no se comprende del todo. Se ha estudiado la transposición por mecanismos pericíclicos. (es)
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