Unusual Closure of the Ten-Vertex Nido Cage via Alkylation: Regiospecific Synthesis of 3-Alkyl Derivatives of closo-1,2-C2B8H10
| Autor: | Mario Bakardjiev, Bohumil Štíbr, Josef Holub, Oleg L. Tok |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Halide Alkylation 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound Bromide Yield (chemistry) Vertex (curve) Physical and Theoretical Chemistry Cage Alkyl Tetrahydrofuran |
| Zdroj: | Inorganic Chemistry. 57:1368-1372 |
| ISSN: | 1520-510X 0020-1669 |
| Popis: | Alkylation of the [nido-5,6-R12C2B8H9]− anions (where R1 = H and Me) with alkyl halides (RX, where R = primary and secondary alkyls) in boiling tetrahydrofuran (THF) proceeds via unusual H2 elimination, followed by cage closure to give a series of the neutral closo-1,2-R12C2B8H7-3-R derivatives in ∼70–80% yields. In contrast, treatment of the unsubstituted [nido-5,6-C2B8H11]− anion with tert-butyl bromide (t-BuBr) led to the formation of the parent closo-1,2-C2B8H10 in >85% yield. The constitution of all compounds isolated has been confirmed unambiguously by multinuclear (11B, 1H, and 13C) nuclear magnetic resonance measurements and α-shift correlation assessments. |
| Databáze: | OpenAIRE |
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