%0 Journal Article %J Carbohydrate Research %D 2018 %T Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: does the reaction proceed through 'axial rich' conformation? %A Sarkar, Nitai %A Sardessai, Richa S. %A Shashidhar, Mysore S. %A Tamboli, Majid I. %A Gonnade, Rajesh G. %X 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. %B Carbohydrate Research %V 463 %P 32-36 %8 JUL %G eng %9 Article %3 Foreign %4 2.096 %R 10.1016/j.carres.2018.04.014