Temperature Dependence of the Reduction of Phthalic Thioanhydrides by NaBH4: Competition between 3??Hydroxythiolactone and Phthalide Formation
…, L Lutsen, D Vanderzande, J Gelan
Index: Polec, Iwona; Lutsen, Laurence; Vanderzande, Dirk; Gelan, Jan European Journal of Organic Chemistry, 2002 , # 6 p. 1033 - 1036
Full Text: HTML
Citation Number: 6
Abstract
Abstract The reduction of phthalic thioanhydrides with NaBH 4 at between 0 and− 20 C 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 γ- ...
Related Articles:
Studies on the Flash Vacuum Thermolysis of Thiones of Selected N??, O??, and S??Heterocycles
[Drewnowski, Tomasz; Lesniak, Stanislaw; Mloston, Grzegorz; Siedlecka, Renata; Skarzewski, Jacek Helvetica Chimica Acta, 2006 , vol. 89, # 5 p. 991 - 999]
[McDonald, Robert S.; Patterson, Patricia; Stevens-Whalley, Ann Canadian Journal of Chemistry, 1983 , vol. 61, p. 1846 - 1852]
Preparative Method for 4-Aryl-and 4-Alkyl-2-thiolenones
[Kagabu, Shinzo; Kaku, Itone Bioscience, Biotechnology, and Biochemistry, 1993 , vol. 57, # 11 p. 1899 - 1901]
A new convenient method for preparation of condensed aromatic and heterocyclic thiolactones
[Vegh; Morel; Decroix; Zalupsky Synthetic Communications, 1992 , vol. 22, # 14 p. 2057 - 2061]
A new convenient method for preparation of condensed aromatic and heterocyclic thiolactones
[Vegh; Morel; Decroix; Zalupsky Synthetic Communications, 1992 , vol. 22, # 14 p. 2057 - 2061]