Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/11475
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dc.contributor.authorVAN MIERLOO, Sarah-
dc.contributor.authorADRIAENSENS, Peter-
dc.contributor.authorMAES, Wouter-
dc.contributor.authorLUTSEN, Laurence-
dc.contributor.authorCLEIJ, Thomas-
dc.contributor.authorBotek, Edith-
dc.contributor.authorChampagne, Benoit-
dc.contributor.authorVANDERZANDE, Dirk-
dc.date.accessioned2011-01-09T08:47:51Z-
dc.date.availableNO_RESTRICTION-
dc.date.available2011-01-09T08:47:51Z-
dc.date.issued2010-
dc.identifier.citationJOURNAL OF ORGANIC CHEMISTRY, 75 (21). p. 7202-7209-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/1942/11475-
dc.description.abstractA convenient and efficient three-step route toward both symmetrically and asymmetrically functionalized 4H-cyclopenta[2,1-b:3,4-b']dithiophenes has been developed. Using this method a broad collection of functionalized bridged bithiophenes can smoothly be accessed. Starting from 3-bromo2,2'-bithiophene, prepared by Kumada coupling of 2-thienylmagnesium bromide with 2,3-dibromothiophene under Pd(dppf)Cl-2 catalysis, lithiation and subsequent reaction with dialkyl ketones afforded (a)symmetrically dialkylated tertiary alcohol derivatives. By means of final Friedel Crafts dehydration cyclization in sulfuric acid medium, these derivatives were converted to 4,4-dialkyl-4H-cyclopenta[2,1-b:3,4-b']dithiophenes. Upon replacement of the alkyl ketone reagent by ethyl levulinate, an ester-functionalized 4H-cyclopenta[2,1-b:3,4-b']dithiophene was prepared, representing an attractive precursor for variously functionalized cyclopentadithiophene compounds.-
dc.description.sponsorshipThe authors gratefully acknowledge the IWT (Institute for the Promotion of Innovation by Science and Technology in Flanders) for the financial support via the SBO-project 060843 "PolySpec". We also thank BELSPO in the frame of the IAP P6/27 network and the FWO (Fund for Scientific Research - Flanders) via the project G.0091.07N for their financial support. We further thank the EU for the FP6 Marie-Curie-RTN "SolarNtype" (MRTN-CT-2006-035533). E.B. thanks IAP program no. P6-27 for her postdoctoral grant. The calculations were performed on the Interuniversity Scientific Computing Facility (iSCF), installed at the Facultes Universitaires Notre-Dame de la Paix (FUNDP, Belgium), for which the authors gratefully acknowledge the financial support of the F.R.S.-FRFC for the convention no. 2.4.617.07.F and of the FUNDP.-
dc.language.isoen-
dc.publisherAMER CHEMICAL SOC-
dc.titleA Three-Step Synthetic Approach to Asymmetrically Functionalized 4H-Cyclopenta[2,1-b:3,4-b ']dithiophenes-
dc.typeJournal Contribution-
dc.identifier.epage7209-
dc.identifier.issue21-
dc.identifier.spage7202-
dc.identifier.volume75-
local.format.pages8-
local.bibliographicCitation.jcatA1-
dc.description.notes[Van Mierloo, Sarah; Adriaensens, Peter J.; Maes, Wouter; Cleij, Thomas J.; Vanderzande, Dirk J.] Hasselt Univ, Inst Mat Res IMO, B-3590 Diepenbeek, Belgium. [Maes, Wouter] Katholieke Univ Leuven, Dept Chem, B-3001 Louvain, Belgium. [Lutsen, Laurence; Vanderzande, Dirk J.] IMEC, Div IMOMEC, B-3590 Diepenbeek, Belgium. [Botek, Edith; Champagne, Benoit] Fac Univ Notre Dame Paix, Chim Theor Lab, B-5000 Namur, Belgium. dirk.vanderzande@uhasselt.be-
local.type.refereedRefereed-
local.type.specifiedArticle-
dc.bibliographicCitation.oldjcatA1-
dc.identifier.doi10.1021/jo101405j-
dc.identifier.isi000283531100018-
item.fulltextNo Fulltext-
item.fullcitationVAN MIERLOO, Sarah; ADRIAENSENS, Peter; MAES, Wouter; LUTSEN, Laurence; CLEIJ, Thomas; Botek, Edith; Champagne, Benoit & VANDERZANDE, Dirk (2010) A Three-Step Synthetic Approach to Asymmetrically Functionalized 4H-Cyclopenta[2,1-b:3,4-b ']dithiophenes. In: JOURNAL OF ORGANIC CHEMISTRY, 75 (21). p. 7202-7209.-
item.contributorVAN MIERLOO, Sarah-
item.contributorADRIAENSENS, Peter-
item.contributorMAES, Wouter-
item.contributorLUTSEN, Laurence-
item.contributorCLEIJ, Thomas-
item.contributorBotek, Edith-
item.contributorChampagne, Benoit-
item.contributorVANDERZANDE, Dirk-
item.validationecoom 2011-
item.accessRightsClosed Access-
crisitem.journal.issn0022-3263-
crisitem.journal.eissn1520-6904-
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