Abstract
2-Hydroxy-5-alkylhexahydro-4H-oxireno[2,3-e]isoindole-4,6(5H)-diones were synthesized, and their C-2 selective ring-opening products were obtained through nucleophilic additions such as with MeOH. The methoxydiols obtained from the ring-opening reactions were converted to corresponding acetate derivatives. The structures of the methoxydiacetates were determined by 1H and 13C NMR and X-ray analyses. Furthermore, theoretical computations were carried out to explain the regioselectivity in the ring-opening reaction of epoxy alcohols. The theoretical calculations showed that the ring-opening reaction of epoxy alcohols proceeds in a thermodynamically controlled manner and regioselectivity occurs depending on the stability of the intermediate.
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Acknowledgements
The author is grateful to Dr. Ertan Sahin, Dr. Yunus Kara, Dr. Hasan Seçen, and Dr. Abdurrahman Atalay for their valuable contributions and Atatürk University for some of the spectroscopic analysis.
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Gündoğdu, Ö. Synthesis of new trisubstituted hexahydro-isoindole-1,3-dione derivatives regio- and stereoselectivity: spectroscopic and theoretical studies. Chem. Pap. 77, 2679–2687 (2023). https://doi.org/10.1007/s11696-022-02657-4
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DOI: https://doi.org/10.1007/s11696-022-02657-4