Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/2491
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dc.contributor.authorPOLEC, Iwona-
dc.contributor.authorLUTSEN, Laurence-
dc.contributor.authorVANDERZANDE, Dirk-
dc.contributor.authorGELAN, Jan-
dc.date.accessioned2007-11-15T08:06:54Z-
dc.date.available2007-11-15T08:06:54Z-
dc.date.issued2002-
dc.identifier.citationEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (6). p. 1033-1036-
dc.identifier.issn1434-193X-
dc.identifier.urihttp://hdl.handle.net/1942/2491-
dc.description.abstractThe reduction of phthalic thioanhydrides with NaBH4 at between 0 and -20 degreesC leads to the selective formation of 3-hydroxy-2-thiophthalides, whereas higher temperatures favour the formation of the corresponding phthalide derivatives. A mechanism is proposed that can explain these observations. Kinetic control at low temperatures leads to an improved stability of the intermediate alkoxide, thus allowing isolation of the gamma-hydroxythiolactone after subsequent acidification of the reaction mixture. In this way the formation of the thermodynamically favoured phthalide derivative is avoided. Further reduction of the gamma-hydroxythiolactone with AcOH/57% aqueous HI yields 2-thiophthalides, useful precursors for conducting polymers. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.-
dc.language.isoen-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.subject.othersulfur heterocycles; reduction; lactones-
dc.titleTemperature dependence of the reduction of phthalic thioanhydrides by NaBH4: Competition between 3-hydroxythiolactone and phthalide formation-
dc.typeJournal Contribution-
dc.identifier.epage1036-
dc.identifier.issue6-
dc.identifier.spage1033-
local.format.pages4-
local.bibliographicCitation.jcatA1-
dc.description.notesUniv Limburg, Mat Res Inst, Div Chem, B-3590 Diepenbeek, Belgium.Vanderzande, D, Univ Limburg, Mat Res Inst, Div Chem, Univ Campus, B-3590 Diepenbeek, Belgium.-
local.type.refereedRefereed-
local.type.specifiedArticle-
dc.bibliographicCitation.oldjcatA1-
dc.identifier.doi10.1002/1099-0690(200203)2002:6<1033::AID-EJOC1033>3.0.CO;2-S-
dc.identifier.isi000174531400009-
item.fulltextNo Fulltext-
item.accessRightsClosed Access-
item.validationecoom 2003-
item.fullcitationPOLEC, Iwona; LUTSEN, Laurence; VANDERZANDE, Dirk & GELAN, Jan (2002) Temperature dependence of the reduction of phthalic thioanhydrides by NaBH4: Competition between 3-hydroxythiolactone and phthalide formation. In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (6). p. 1033-1036.-
item.contributorLUTSEN, Laurence-
item.contributorPOLEC, Iwona-
item.contributorVANDERZANDE, Dirk-
item.contributorGELAN, Jan-
crisitem.journal.issn1434-193X-
crisitem.journal.eissn1099-0690-
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