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- Publisher Website: 10.1021/jo971112k
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Article: Catalytic Dehalogenation of Highly Chlorinated Benzenes and Aroclors Using PdCl2(dppf) and NaBH4: Efficiency, Selectivity, and Base Support
Title | Catalytic Dehalogenation of Highly Chlorinated Benzenes and Aroclors Using PdCl2(dppf) and NaBH4: Efficiency, Selectivity, and Base Support |
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Authors | |
Issue Date | 1998 |
Citation | Journal of Organic Chemistry, 1998, v. 63, n. 11, p. 3538-3543 How to Cite? |
Abstract | Reported herein is a convenient one-pot system that can dehalogenate highly chlorinated benzenes at room temperature with reasonable conversion rates using PdCl2(dppf) (dppf = 1,1′-bis-(diphenylphosphino)ferrocene) as catalyst, NaBH4 as reducing agent, TMEDA (N,N,N',N'-tetra-methyl-1,2-ethylenediamine) as supporting base, and THF as solvent. Total conversion of substrate to less chlorinated isomers is achieved within 200 h when hexachloro-, pentachloro-, and tetrachlorobenzenes are used. Degradation to benzene is not achievable, but the efficiency shown in the partial dechlorination is encouraging. A pronounced selectivity is accomplished with removal of meta-substituted chlorines being preferred over ortho- or para-substituted Cl atoms. The sequence in which reagents are added is also critical, thus indicating a protective role of the base. The effectiveness of the method was tested on the PCB mixtures Aroclor 1242, 1248, and 1254. Dechlorination efficiency at 67 °C is satisfactory. |
Persistent Identifier | http://hdl.handle.net/10722/219350 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Lassová, Luisa | - |
dc.contributor.author | Lee, Hian Kee | - |
dc.contributor.author | Hor, T. S Andy | - |
dc.date.accessioned | 2015-09-23T02:56:51Z | - |
dc.date.available | 2015-09-23T02:56:51Z | - |
dc.date.issued | 1998 | - |
dc.identifier.citation | Journal of Organic Chemistry, 1998, v. 63, n. 11, p. 3538-3543 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10722/219350 | - |
dc.description.abstract | Reported herein is a convenient one-pot system that can dehalogenate highly chlorinated benzenes at room temperature with reasonable conversion rates using PdCl2(dppf) (dppf = 1,1′-bis-(diphenylphosphino)ferrocene) as catalyst, NaBH4 as reducing agent, TMEDA (N,N,N',N'-tetra-methyl-1,2-ethylenediamine) as supporting base, and THF as solvent. Total conversion of substrate to less chlorinated isomers is achieved within 200 h when hexachloro-, pentachloro-, and tetrachlorobenzenes are used. Degradation to benzene is not achievable, but the efficiency shown in the partial dechlorination is encouraging. A pronounced selectivity is accomplished with removal of meta-substituted chlorines being preferred over ortho- or para-substituted Cl atoms. The sequence in which reagents are added is also critical, thus indicating a protective role of the base. The effectiveness of the method was tested on the PCB mixtures Aroclor 1242, 1248, and 1254. Dechlorination efficiency at 67 °C is satisfactory. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of Organic Chemistry | - |
dc.title | Catalytic Dehalogenation of Highly Chlorinated Benzenes and Aroclors Using PdCl2(dppf) and NaBH4: Efficiency, Selectivity, and Base Support | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jo971112k | - |
dc.identifier.scopus | eid_2-s2.0-0000465248 | - |
dc.identifier.volume | 63 | - |
dc.identifier.issue | 11 | - |
dc.identifier.spage | 3538 | - |
dc.identifier.epage | 3543 | - |
dc.identifier.isi | WOS:000074172100007 | - |
dc.identifier.issnl | 0022-3263 | - |