Study of the controlled temperature reaction between closo-decahydrodecaborate and alcohols in H2SO4 medium
| Autor: | Fatima Abi-Ghaida, Ahmad Mehdi, Suzan Al Anwar, Sami Tlais, Rabih Jahjah, Zahra Laila, Riman Aoun, Daoud Naoufal, Ogaritte Yazbeck |
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| Rok vydání: | 2015 |
| Předmět: | |
| Zdroj: | Main Group Chemistry. 14:301-312 |
| ISSN: | 1745-1167 1024-1221 |
| DOI: | 10.3233/mgc-150173 |
| Popis: | The reactions of the ammonium salt of closo-decahydrodecaborate (NH4)2B10H10 with alcohols were studied in concentrated sulfuric acid medium. Alcohols ROH (R = CH3 ,C 2H5 ,C 3H7, iso-C3H7 ,C 4H9, 2-C4H9, ter-C4H9, C5H11) played the role of solvent and ligand, simultaneously. These Electrophile Induced Nucleophilic Substitution Reactions were conducted at two different temperatures (25 ◦ C or reflux) in atmospheric air and produced (2-B10H9OR) 2− , (2,7(8)-B10H8(OR)2) 2- and/or (B10H7(OR)3) 2- . The rate of the reaction and the nature of the product formed depended on the temperature, on the alcohol, and on the reaction duration. The reactions at 25 ◦ C, if proceeded, produced mainly the monoalkoxy derivative, (2-B10H9OR) 2- . For the longer chain alcohols (4 carbons and above) the increase in the reaction duration and the temperature resulted in higher substitution, thus producing the dialkoxy (2,7(8)-B10H8(OR)2) 2- and trialkoxy (B10H7(OR)3) 2- derivatives. Meanwhile only the monoalkoxy (2-B10H9OR) 2- plus the dialkyloxonium (2-B10H9OR2) − derivatives were produced with the shorter alcohols (1 to 3 carbons) at refluxing temperature. All these derivatives were isolated in their pure forms on DEAE-cellulose column with adequate yields, and characterized by 11 B, 13 C, 1 H NMR, negative ESI and TLC. |
| Databáze: | OpenAIRE |
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