Baker-Venkataraman rearrangement
- Baker-Venkataraman rearrangement
The Baker-Venkataraman rearrangement is the chemical reaction of 2-acetoxyacetophenones with base to form 1,3-diketones.[cite journal | last = Baker | first = W. | journal = J. Chem. Soc. | date = 1933 | pages = 1381–1389 | doi = 10.1039/JR9330001381 | title = Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones ] ][cite journal | author = Mahal, H. S.; Venkataraman, K. | journal = J. Chem. Soc. | date = 1934 | pages = 1767–1769 | doi = 10.1039/JR9340001767 | title = Synthetical experiments in the chromone. group. XIV. Action of sodamide on 1-acyloxy-2-acetonaphthones ] ]This rearrangement reaction proceeds via enolate formation followed by acyl transfer.
The Baker-Venkataraman rearrangement is often used to synthesize chromones and flavones.[cite journal | author = T. S. Wheeler | title = Flavone | journal = Organic Syntheses | url = http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0478 | volume = 32 | pages = 72 | date = 1952 "(also in the [http://www.orgsyn.org/orgsyn/pdfs/cv4p0478.pdf Collective Volume (1963) 4:478 (PDF)] )."] [cite journal | last = Jain | first = P. K. | coauthors ="et al." | journal = Synthesis | date = 1982 | pages = 221–222 | doi = 10.1055/s-1982-29755 | title = A Facile Baker-Venkataraman Synthesis of Flavones using Phase Transfer Catalysis ] [cite journal | author = Kalinin, A. V.;Da Silva, A. J. M.;Lopes, C. C.;Lopes, R. S. C.;Snieckus, V. | journal = Tetrahedron Lett. | date = 9 July 1998 | volume = 39 | issue = 28 | pages = 4995–4998 | doi = 10.1016/S0040-4039(98)00977-0 | title = Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins ] ]References
ee also
*Allan-Robinson reaction
*Kostanecki acylation
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Baker-Venkataraman-Umlagerung — Die Baker Venkataraman Umlagerung ist eine Reaktion aus der organischen Chemie. Sie dient der Synthese von 1,3 Diketon substituierten Derivaten des Phenols. Ausgegangen wird hierbei von einem acylierten Phenolderivat. Die Reaktion ist nach ihren… … Deutsch Wikipedia
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Flavone (groupe) — La flavone (2 phénylchromén 4 one), squelette de base des flavones Les flavones (du latin flavus, jaune) sont une sous famille des flavonoïdes dont la structure est basée sur la flavone (2 phényl 1 benzopyran 4 one ou 2 phénylchromén 4 one). Ce… … Wikipédia en Français
Réaction d'Allan-Robinson — La réaction d Allan Robinson est la réaction chimique d une o hydroxyphénone avec un anhydride aromatique (anydride benzoïque par exemple) pour former une flavone (ou une isoflavone)[1],[2],[3] … Wikipédia en Français
