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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 | Source: | 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. | Keywords: | sulfur heterocycles; reduction; lactones | Document URI: | http://hdl.handle.net/1942/2491 | ISSN: | 1434-193X | e-ISSN: | 1099-0690 | DOI: | 10.1002/1099-0690(200203)2002:6<1033::AID-EJOC1033>3.0.CO;2-S | ISI #: | 000174531400009 | Category: | A1 | Type: | Journal Contribution | Validations: | ecoom 2003 |
Appears in Collections: | Research publications |
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