Catalytic Intermolecular Aldehyde-Ketone Coupling via Acyl Phosphonates

Date

2009-03-06

Author

Demir, Ayhan Gürbüz
Gollu, Mehmet
Reis, Oemer

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

130
views

0
downloads

The first catalytic intermolecular aldehyde-ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate-phosphate rearrangement. These anions readily react with activated ketones to form acyloin type coupling in 41-95% yields.

Subject Keywords

Nucleophilic acylation, Donor, Rearrangement, Acylphosphonates, Benzoin reactions, Anion equivalents

URI

https://hdl.handle.net/11511/62945

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo8026627

Collections

Department of Educational Sciences, Article

Suggestions

OpenMETU
Core

Catalytic conversion of methane to methanol on Cu-SSZ-13 using N2O as oxidant İpek Torun, Bahar (2016-01-01) Direct catalytic methanol production from methane is achieved on Cu-SSZ-13 zeolite catalysts using N2O as the oxidant. The methanol production rate on Cu-SSZ-13 (on a per gram basis) was more than twice the rate on Cu-mordenite and more than four times the rate on Cu-ZSM-5.
ELECTROINITIATED POLYMERIZATION OF BIS(TRIBROMOPHENOXO)-N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE COPPER(II) COMPLEX Akbulut, Ural; KISAKUREK, D; Toppare, Levent Kamil (Wiley, 1990-01-01) Tribromophenol copper(II) complexes with ligands such as pyridine and ethylenediamine are known to polymerize thermally. Generally, high temperature is required for thermal polymerization of such complexes. Thermal polymerization of trihalophenol copper(II) complexes in toluene has an induction period of c. 30 min. Electroinitiated polymerization of trihalophenol copper(II) complexes has also been accomplished recently using pyridine or ethylenediamine as ligands. However, the above mentioned copper(II) com...
Catalytic combustion of ethyl acetate GÜRMEN ÖZÇELİK, TUĞBA; Atalay, Sueheyda; Alpay, Erden (Elsevier BV, 2007-01-01) The catalytic combustion of ethyl acetate over prepared metal oxide catalysts was investigated. CeO, Co2O3, Mn2O3, Cr2O3, and CeO-Co2O3 catalysts were prepared on monolith supports and they were tested. Before conducting the catalyst experiments, we searched for the homogeneous gas phase combustion reaction of ethylacetate. According to the homogeneous phase experimental results, 45% of ethylacetate was converted at the maximum reactor temperature tested (350 degrees C). All the prepared catalysts were test...
Reaction network of indole hydrodenitrogenation over NiMoS/γ-Al2O3 catalysts BUNCH, Abdu; ZHANG, Liping; Karakaş, Gürkan; Ozkan, Umit S. (2000-01-03) The reaction network of indole hydrodenitrogenation (HDN) was investigated over gamma-Al2O3 supported NiMo sulfide catalysts in an effort to acquire a fundamental understanding of the different reaction pathways in the mechanism. Experiments were performed primarily at 1000 psig, using a wide range of temperatures and feed concentrations. The effect of H2S on different reaction Steps of the network was also investigated. Two major pathways were proposed to account for the formation of ethylcyclohexane (ECH)...
Fungal deracemization of benzoin Demir, AS; Hamamcı, Haluk; Sesenoglu, O; Neslihanoglu, R; Asikoglu, B; Capanoglu, D (2002-09-02) An enzyme system of Rhizopus oryzae (ATCC 9363) catalyzes the inversion of the chirality of benzoin via a deracemization reaction and, depending on the pH of the medium, both enantiomers of benzoin are obtained in good yield and high ee starting from rac-benzoin.

Citation Formats

A. G. Demir, M. Gollu, and O. Reis, “Catalytic Intermolecular Aldehyde-Ketone Coupling via Acyl Phosphonates,” JOURNAL OF ORGANIC CHEMISTRY, pp. 2197–2199, 2009, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62945.