Reaction of dibutyltin oxide with amides in presence of traces of water: multinuclear NMR study and mechanism
| Autor: | Marie-France Llauro, Jérôme Gimenez, A. Michel, Roger Petiaud |
|---|---|
| Rok vydání: | 1999 |
| Předmět: |
Dibutyltin oxide
Transamidification Organic Chemistry chemistry.chemical_element Reactive extrusion Biochemistry Stannoxane Inorganic Chemistry Hydrolysis chemistry.chemical_compound chemistry Amide Polymer chemistry Materials Chemistry Anhydrous Organic chemistry Physical and Theoretical Chemistry Tin |
| Zdroj: | Journal of Organometallic Chemistry. 575:286-300 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/s0022-328x(98)01008-0 |
| Popis: | The product of the reaction of primary and secondary amides with dibutyltin oxide is shown to be a dimeric 1,3-diacyloxytetrabutyldistannoxane. The reaction was studied in bulk with model amides at 180°C, avoiding perfect anhydrous conditions, in view to be transposable to transamidification with reactive extrusion process. The formation of an intermediate compound of the type 1-acyloxy-3-alkylaminotetrabutyldistannoxane is pointed out. With an excess of amide, the presence of water leads to the dimeric 1,3-diacyloxytetrabutyldistannoxane. Without an excess of amide, the hydrolysis of this intermediate leads to a more complex tetrastannoxane structure associated in a more or less perfect ladder-like structure including partially hydrolyzed and condensed forms of the distannoxane. The dimeric 1-acyloxy-3-alkoxytetrabutyldistannoxanes resulting from the reaction of esters with dibutyltin oxide are shown to give a similar stannoxane structure after hydrolysis. All the products were characterized in solution by 1 H-, 13 C- and 119 Sn-NMR spectroscopy. On the basis of the spectroscopic analysis, a mechanism of the reaction is proposed and discussed. |
| Databáze: | OpenAIRE |
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