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Collect. Czech. Chem. Commun. 2007, 72, 715-727
https://doi.org/10.1135/cccc20070715

The Mechanism of the Permanganate-Promoted Oxidative Cyclization of 1,5-Dienes - a DFT Study

Alexander Poethig and Thomas Strassner*

Professur für Physikalische Organische Chemie, Technische Universität Dresden, 01062 Dresden, Germany

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  • Hussein Aqeel A., Jafar Nadhir N. A., Ma Yumiao: Elucidating the Mechanism of Tetrahydrofuran-Diol Formation through Os(VI)-Catalyzed Oxidative Cyclization of 5,6-Dihydroxyalkenes Ligated by Citric Acid. J. Org. Chem. 2024, 89, 6892. <https://doi.org/10.1021/acs.joc.4c00268>
  • Hussein Aqeel A.: Ru-catalysed oxidative cyclisation of 1,5-dienes: an unprecedented role for the co-oxidant. RSC Adv. 2020, 10, 15228. <https://doi.org/10.1039/D0RA02303E>
  • Hussein Aqeel A., Phipps Maximillian J. S., Skylaris Chris-Kriton, Brown Richard C. D.: Mechanism of Os-Catalyzed Oxidative Cyclization of 1,5-Dienes. J. Org. Chem. 2019, 84, 15173. <https://doi.org/10.1021/acs.joc.9b02174>
  • Luo Qiuhan, Shi Zhijun, Li Dingxiong, Zhu Caizhen, Wang Mingliang: DFT study on the ionic cyclization mechanism of copolymers of acrylonitrile-itaconic acid: Direct or autocatalytic?. Chemical Physics Letters 2017, 687, 158. <https://doi.org/10.1016/j.cplett.2017.09.011>
  • Adrian Juliane, Gross Leona J, Stark Christian B W: The direct oxidative diene cyclization and related reactions in natural product synthesis. Beilstein J. Org. Chem. 2016, 12, 2104. <https://doi.org/10.3762/bjoc.12.200>
  • Sheikh Nadeem S.: Stereoselective synthesis of trans-THF rings using an oxidative cyclisation-radical deoxygenation sequence: application to the formal synthesis of trans-(2R,5R)-linalool oxide. RSC Adv. 2015, 5, 3941. <https://doi.org/10.1039/C4RA13258K>
  • Al Hazmi Ali M., Sheikh Nadeem S., Bataille Carole J. R., Al-Hadedi Azzam A. M., Watkin Sam V., Luker Tim J., Camp Nicholas P., Brown Richard C. D.: trans-2-Tritylcyclohexanol as a Chiral Auxiliary in Permanganate-Mediated Oxidative Cyclization of 2-Methylenehept-5-enoates: Application to the Synthesis of trans-(+)-Linalool Oxide. Org. Lett. 2014, 16, 5104. <https://doi.org/10.1021/ol502454r>
  • Sheikh Nadeem S.: Comparative perspective and synthetic applications of transition metal mediated oxidative cyclisation of 1,5-dienes towards cis-2,5-disubstituted tetrahydrofurans. Org. Biomol. Chem. 2014, 12, 9492. <https://doi.org/10.1039/C4OB01491J>
  • Piccialli Vincenzo: Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species. Molecules 2014, 19, 6534. <https://doi.org/10.3390/molecules19056534>
  • Javan Marjan Jebeli, Tehrani Zahra Aliakbar, Fattahi Alireza, Hashemi Mohammad Mahmoodi: How hydrogen‐bonded MnO4‐ can influence oxidation of olefins in both gas phase and solution?. J of Physical Organic Chem 2012, 25, 1198. <https://doi.org/10.1002/poc.2992>
  • Poethig Alexander, Strassner Thomas: Stereoselective OsO4-Catalyzed Oxidative Cyclization of 1,5-Dienes. J. Org. Chem. 2010, 75, 1967. <https://doi.org/10.1021/jo100147e>
  • Sheikh Nadeem S., Bataille Carole J., Luker Tim J., Brown Richard C. D.: Enantioselective Formal Synthesis of Eurylene: Synthesis of the cis- and trans-THF Fragments Using Oxidative Cyclization. Org. Lett. 2010, 12, 2468. <https://doi.org/10.1021/ol100513y>