Reductive debromination of decabromodiphenyl ether yields brominated dibenzofurans in a Pschorr-type cyclisation
作者： Grzegorz Rotko , Piotr P. Romańczyk , Stefan S. Kurek
DOI: 10.1016/J.ELECOM.2013.10.010
关键词:
摘要: Abstract Brominated dibenzofurans are readily produced from decabromodiphenyl ether by a Pschorr-type cyclisation upon reductive debromination in the absence of good H-donors. DFT-D calculations confirmed that, for polybrominated diphenyl ethers, reaction is strongly favoured both kinetically and thermodynamically.
sci-hub.se 参考文章(25)
Mohammednoor Altarawneh, Bogdan Z. Dlugogorski, A mechanistic and kinetic study on the formation of PBDD/Fs from PBDEs. Environmental Science & Technology. ,vol. 47, pp. 5118- 5127 ,(2013) , 10.1021/ES305081J
E. Cancès, B. Mennucci, J. Tomasi, A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics Journal of Chemical Physics. ,vol. 107, pp. 3032- 3041 ,(1997) , 10.1063/1.474659
Pascale M.L. Bonin, Patrick Edwards, Dorin Bejan, Chun Chi Lo, Nigel J. Bunce, Alexandre D. Konstantinov, Catalytic and electrocatalytic hydrogenolysis of brominated diphenyl ethers Chemosphere. ,vol. 58, pp. 961- 967 ,(2005) , 10.1016/J.CHEMOSPHERE.2004.09.099
Stefan Grimme, Semiempirical GGA-type density functional constructed with a long-range dispersion correction. Journal of Computational Chemistry. ,vol. 27, pp. 1787- 1799 ,(2006) , 10.1002/JCC.20495
Mohammad S. Mubarak, Dennis G. Peters, Electrochemical reduction of di-, tri-, and tetrahalobenzenes at carbon cathodes in dimethylformamide Evidence for a halogen dance during the electrolysis of 1,2,4,5-tetrabromobenzene Journal of Electroanalytical Chemistry. ,vol. 435, pp. 47- 53 ,(1997) , 10.1016/S0022-0728(97)00003-X
Sandor Karady, Jordan M. Cummins, J. J. Dannenberg, Emma del Rio, Peter G. Dormer, Benjamin F. Marcune, Robert A. Reamer, Tomas L. Sordo, Intramolecular aromatic 1,5-hydrogen transfer in free radical reactions III. Reactivity of diaryl ketones, ethers, thioethers, sulfoxydes, and sulfones. An experimental and theoretical study. Organic Letters. ,vol. 5, pp. 1175- 1178 ,(2003) , 10.1021/OL027301T
F. F. Gadallah, A. A. Cantu, R. M. Elofson, Pschorr reaction by electrochemical generation of free radicals. II. Benzophenone series. Alternative mechanism Journal of Organic Chemistry. ,vol. 38, pp. 2386- 2393 ,(1973) , 10.1021/JO00953A023
Shileen Donnelly, James Grimshaw, Jadwiga Trocha-Grimshaw, Cyclizations. Part 3. Use of a mild-steel cathode in the electrochemical intramolecular cyclization of aryl halides Electrochimica Acta. ,vol. 41, pp. 489- 492 ,(1996) , 10.1016/0013-4686(95)00334-7
Abdirisak A. Isse, Patrizia R. Mussini, Armando Gennaro, New Insights into Electrocatalysis and Dissociative Electron Transfer Mechanisms: The Case of Aromatic Bromides Journal of Physical Chemistry C. ,vol. 113, pp. 14983- 14992 ,(2009) , 10.1021/JP904797M
T. Guena, L. Wang, M. Gattrell, B. MacDougall, Mediated Approach for the Electrochemical Reduction of Chlorobenzenes in Nonaqueous Media Journal of The Electrochemical Society. ,vol. 147, pp. 248- 255 ,(2000) , 10.1149/1.1393183