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Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/2491

Title: Temperature dependence of the reduction of phthalic thioanhydrides by NaBH4: Competition between 3-hydroxythiolactone and phthalide formation
Authors: POLEC, Iwona
LUTSEN, Laurence
VANDERZANDE, Dirk
GELAN, Jan
Issue Date: 2002
Publisher: WILEY-V C H VERLAG GMBH
Citation: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (6). p. 1033-1036
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.
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.
URI: http://hdl.handle.net/1942/2491
DOI: 10.1002/1099-0690(200203)2002:6<1033::AID-EJOC1033>3.0.CO;2-S
ISI #: 000174531400009
ISSN: 1434-193X
Category: A1
Type: Journal Contribution
Validation: ecoom, 2003
Appears in Collections: Research publications

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