Abstract:
A new type of dimerization of 2-arylcyclopropane-1,1-dicarboxylates in the presence of anhydrous GaCl3 to give acyclic dimers, viz., substituted pent-2-ene-1,1,5,5-tetracarboxylates, occurs at room temperature. In this reaction, one molecule of the donor–acceptor cyclopropane manifests a non-classical reactivity and serves as a 1,2-dipole.
Citation:
R. A. Novikov, A. V. Tarasova, Yu. V. Tomilov, “GaCl3-mediated acyclic dimerization of donor–acceptor cyclopropanes using 1,2-dipole reactivity”, Mendeleev Commun., 25:5 (2015), 341–343
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https://www.mathnet.ru/eng/mendc2401
https://www.mathnet.ru/eng/mendc/v25/i5/p341
This publication is cited in the following 16 articles:
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Dongyang Wang, Jing Zhao, Jun Chen, Qing Xu, Huan Li, “Intramolecular Arylative Ring Opening of Donor‐Acceptor Cyclopropanes in the Presence of Triflic Acid: Synthesis of 9H‐Fluorenes and 9,10‐Dihydrophenanthrenes”, Asian J Org Chem, 8:11 (2019), 2032
Roman A. Novikov, Denis D. Borisov, Anna V. Tarasova, Yaroslav V. Tkachev, Yury V. Tomilov, “Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes”, Angew Chem Int Ed, 57:32 (2018), 10293
Roman A. Novikov, Denis D. Borisov, Anna V. Tarasova, Yaroslav V. Tkachev, Yury V. Tomilov, “Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes”, Angewandte Chemie, 130:32 (2018), 10450
Olga A. Ivanova, Alexey O. Chagarovskiy, Alexey N. Shumsky, Vasiliy D. Krasnobrov, Irina I. Levina, Igor V. Trushkov, “Lewis Acid Triggered Vinylcyclopropane–Cyclopentene Rearrangement”, J. Org. Chem., 83:2 (2018), 543
R. A. Novikov, D. D. Borisov, Yu. V. Tomilov, “Lewis acid-mediated reactions of donor-acceptor cyclopropanes with diazo esters”, Russ Chem Bull, 67:2 (2018), 265
Yu. V. Tomilov, L. G. Menchikov, R. A. Novikov, O. A. Ivanova, I. V. Trushkov, “Methods for the synthesis of donor-acceptor cyclopropanes”, Russian Chem. Reviews, 87:3 (2018), 201–250
Maxime Dousset, Jean‐Luc Parrain, Gaëlle Chouraqui, “Intriguing Electrophilic Reactivity of Donor–Acceptor Cyclopropanes: Experimental and Theoretical Studies”, Eur J Org Chem, 2017:35 (2017), 5238
Roman A. Novikov, Anna V. Tarasova, Dmitry A. Denisov, Denis D. Borisov, Victor A. Korolev, Vladimir P. Timofeev, Yury V. Tomilov, “[4 + 2] Annulation of Donor–Acceptor Cyclopropanes with Acetylenes Using 1,2-Zwitterionic Reactivity”, J. Org. Chem., 82:5 (2017), 2724
Denis D. Borisov, Roman A. Novikov, Yury V. Tomilov, “Highly diastereoselective formation of 3,7-dioxabicyclo[3.3.0]octan-2-ones in reaction of 2-arylcyclopropanedicarboxylates with aromatic aldehydes using 1,2-zwitterionic reactivity type”, Tetrahedron Letters, 58:38 (2017), 3712
Roman A. Novikov, Anna V. Tarasova, Yury V. Tomilov, “ChemInform Abstract: GaCl3‐Mediated Acyclic Dimerization of Donor—Acceptor Cyclopropanes Using 1,2‐Dipole Reactivity.”, ChemInform, 47:8 (2016)
R. A. Novikov, A. V. Tarasova, D. A. Denisov, V. A. Korolev, Yu. V. Tomilov, “Cascade dimerization of 2-styryl-1,1-cyclopropanedicarboxylate upon treatment with gallium trichloride”, Russ Chem Bull, 65:11 (2016), 2628
Dmitry A. Denisov, Roman A. Novikov, Konstantin V. Potapov, Victor A. Korolev, Evgeny V. Shulishov, Yury V. Tomilov, “1,1 '-Bicyclopropyl-2,2-dicarboxylate and Cyclopropylmethylidenemalonate as Homovinylogs and Vinylogs of Donor-Acceptor Cyclopropanes”, ChemistrySelect, 1:20 (2016), 6374
Thangavel Selvi, Kannupal Srinivasan, “Synthetic Applications of Aroyl‐ and Nitro‐substituted 2‐Aryl‐Cyclopropane‐1,1‐Dicarboxylates”, Israel Journal of Chemistry, 56:6-7 (2016), 454
Denis D. Borisov, Roman A. Novikov, Yury V. Tomilov, “GaCl3‐Mediated Reactions of Donor–Acceptor Cyclopropanes with Aromatic Aldehydes”, Angewandte Chemie, 128:40 (2016), 12421
Denis D. Borisov, Roman A. Novikov, Yury V. Tomilov, “GaCl3‐Mediated Reactions of Donor–Acceptor Cyclopropanes with Aromatic Aldehydes”, Angew Chem Int Ed, 55:40 (2016), 12233
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