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Abstract
Bis(O,O-diisopropoxyphosphinothioyl) diselenide reacts readily and quickly with the sodium salt of malonates to give quantitatively stable sodium 2-(O,O-diisopropyl phosphorothioselenenyl)propanedioates. No traces of the corresponding C,C-diselenenylation products were detected. A standard aqueous workup procedure affords the products, albeit in poor yield (about 45%). It was proved that the reaction is reversible due to the presence of nucleophilic sodium O,O-diisopropylphosphoroselenothioate in the reaction mixture. The reaction conducted with methyl iodide as a coreactant significantly improved the yield of the selenenylated product up to 88%. In contrast to the respective C-(phenylselenenyl)malonate that undergoes thermal disproportionation, the diethyl 2-(O,O-diisopropyl phosphorothioselenenyl)propanedioate is stable and remains unchanged even after prolonged heating in boiling toluene. The mechanism of phosphorothioselenenylation of malonates is described.
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
no. 186,
pages 1483 - 1490,
ISSN: 1042-6507 - Language:
- English
- Publication year:
- 2011
- Bibliographic description:
- Majewski A., Przychodzeń W., Rachoń J.: Efficient Selenenylation of Malonates Using Bis(phosphorothioyl) Diselenide// PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS. -Vol. 186, nr. iss. 7 (2011), s.1483-1490
- DOI:
- Digital Object Identifier (open in new tab) 10.1080/10426507.2010.519253
- Verified by:
- Gdańsk University of Technology
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