Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: does the reaction proceed through 'axial rich' conformation?
| Title | Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: does the reaction proceed through 'axial rich' conformation? |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Sarkar, N, Sardessai, RS, Shashidhar, MS, Tamboli, MI, Gonnade, RG |
| Journal | Carbohydrate Research |
| Volume | 463 |
| Pagination | 32-36 |
| Date Published | JUL |
| Type of Article | Article |
| Abstract | scyllo-Inositol derived 1,2-trans-diequatorial halohydrins can be efficiently converted to the corresponding epoxides in the presence of lithium hydride. The structure of one of the epoxides was determined by single crystal X-ray diffraction analysis. This provides a potential route for the preparation of ring modified inositol derivatives. DFT calculations suggest that this epoxide formation could be proceeding through the intermediacy of the cyclohexane ring-inverted axial-rich conformer (1,2-trans-diaxial halohydrin). This is supported by the results of DFT calculations on the formation of inositol orthoformate, where the product is locked in the axial-rich conformation, while the starting inositol has the equatorial-rich conformation. |
| DOI | 10.1016/j.carres.2018.04.014 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.096 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry