Inductive Hydroxyhalogenation of Bicyclo[2.2.1]heptenes and Synthesis of Amino Alcohols from the Reaction Products
| Autor: | Kh. M. Alimardanov, Sh. I. Ismailova, O. A. Sadygov |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Bicyclic molecule 010405 organic chemistry Chemistry 010401 analytical chemistry Halide General Chemistry 01 natural sciences Medicinal chemistry Heptene 0104 chemical sciences chemistry.chemical_compound Yield (chemistry) Electrophile Dehydrohalogenation Selectivity Alkyl |
| Zdroj: | Russian Journal of General Chemistry. 88:862-868 |
| ISSN: | 1608-3350 1070-3632 |
| DOI: | 10.1134/s1070363218050031 |
| Popis: | A method of synthesis of aminobicycloheptanols by the hydroxyhalogenation of bicyclo[2.2.1]- heptene and its alkyl derivatives in a cycloolefin‒oxidant‒hydrogen halide system to induce electrophilic intermediates followed by substitution of the halogen atoms by amino groups of different compositions and structures. It was found that the selectivity of the reaction depends on the formation/consumption rate ratio for the electrophilic intermediate. A high selectivity with respect to hydroxyhalides takes place, when the consumption rate of the latter intermediate is higher than its formation rate. An increase in the pH of the medium becomes higher than 10.5 decreases the yield of amino alcohols and changes the reaction direction due to acceleration of dehydrohalogenation and formation of the corresponding epoxides. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|