Abstract:
The [4+2]-cycloaddition reaction of quinopimaric acid with thebaine or β-dihydrothebaine has been performed in order to illustrate the importance of preliminary orientation of the diene and dienophile in the reaction complex stabilized due to different factors: salification was shown to be the principal factor in the orientation of the diene and dienophile in aqueous media, and steric factors were found to dominate in hydrocarbon solvents.
Document Type:
Article
Language: English
Citation:
G. A. Tolstikov, E. E. Shults, T. Sh. Malikova, L. V. Spirikhin, “The Importance of Preliminary Orientation in [4+2]-Cycloadditions of Dienes and Dienophiles with Complex Structures”, Mendeleev Commun., 4:2 (1994), 60–62
Linking options:
https://www.mathnet.ru/eng/mendc5153
https://www.mathnet.ru/eng/mendc/v4/i2/p60
This publication is cited in the following 2 articles:
Ewa Dresler, Przemysław Woliński, Aneta Wróblewska, Radomir Jasiński, “On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions between Aryl Azides and Ethyl Propiolate”, Molecules, 28:24 (2023), 8152
E.E. Shults, M.M. Shakirov, G.A. Tolstikov, V.N. Kalinin, G. Schmidhammer, “Thebaine Adducts with Maleimides. Synthesis and Transformations”, Russ J Org Chem, 41:8 (2005), 1132
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