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 TypeJournal Article
Year of Publication2018
AuthorsSarkar, N, Sardessai, RS, Shashidhar, MS, Tamboli, MI, Gonnade, RG
JournalCarbohydrate Research
Volume463
Pagination32-36
Date PublishedJUL
Type of ArticleArticle
Abstractscyllo-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.
DOI10.1016/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

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