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http://hdl.handle.net/1942/2491
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DC Field | Value | Language |
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dc.contributor.author | POLEC, Iwona | - |
dc.contributor.author | LUTSEN, Laurence | - |
dc.contributor.author | VANDERZANDE, Dirk | - |
dc.contributor.author | GELAN, Jan | - |
dc.date.accessioned | 2007-11-15T08:06:54Z | - |
dc.date.available | 2007-11-15T08:06:54Z | - |
dc.date.issued | 2002 | - |
dc.identifier.citation | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (6). p. 1033-1036 | - |
dc.identifier.issn | 1434-193X | - |
dc.identifier.uri | http://hdl.handle.net/1942/2491 | - |
dc.description.abstract | The 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.iso | en | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.subject.other | sulfur heterocycles; reduction; lactones | - |
dc.title | Temperature dependence of the reduction of phthalic thioanhydrides by NaBH4: Competition between 3-hydroxythiolactone and phthalide formation | - |
dc.type | Journal Contribution | - |
dc.identifier.epage | 1036 | - |
dc.identifier.issue | 6 | - |
dc.identifier.spage | 1033 | - |
local.format.pages | 4 | - |
local.bibliographicCitation.jcat | A1 | - |
dc.description.notes | Univ 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.refereed | Refereed | - |
local.type.specified | Article | - |
dc.bibliographicCitation.oldjcat | A1 | - |
dc.identifier.doi | 10.1002/1099-0690(200203)2002:6<1033::AID-EJOC1033>3.0.CO;2-S | - |
dc.identifier.isi | 000174531400009 | - |
item.validation | ecoom 2003 | - |
item.fulltext | No Fulltext | - |
item.fullcitation | POLEC, 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.accessRights | Closed Access | - |
item.contributor | POLEC, Iwona | - |
item.contributor | LUTSEN, Laurence | - |
item.contributor | VANDERZANDE, Dirk | - |
item.contributor | GELAN, Jan | - |
crisitem.journal.issn | 1434-193X | - |
crisitem.journal.eissn | 1099-0690 | - |
Appears in Collections: | Research publications |
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