Abstract:
A selectivity-switched dimerization process for (5-phenyl-2-thienyl)cyclopropane-1,1-dicarboxylate under activation conditions with anhydrous Gaiii salts was developed. Using GaCl3 or Ga(NTf2)3 as catalysts, 3a,4,5a,6,7,8-hexahydro-5H-pentaleno[6a,1-b]thiophene and 5,6-dihydro-4H-cyclo-penta[b]thiophene derivatives can be selectively obtained as a result of ipso-type and [3+2]-annulation type dimerization. The crucial role of a phenyl substituent at position 5 of the thiophene ring and some regularities are discussed.
Citation:
D. D. Borisov, R. A. Novikov, Yu. V. Tomilov, “Gallium(iii)-mediated dimerization routes for (5-phenyl-2-thienyl)cyclopropane-1,1-dicarboxylate”, Mendeleev Commun., 32:2 (2022), 170–172
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https://www.mathnet.ru/eng/mendc602
https://www.mathnet.ru/eng/mendc/v32/i2/p170
This publication is cited in the following 4 articles:
D. D. Borisov, D. A. Knyazev, R. A. Novikov, Yu. V. Tomilov, Mendeleev Commun., 35:1 (2025), 93–95
Yuta Onuki, Koga Yamazaki, Yuto Masuda, Takayuki Yakura, Hisanori Nambu, “Ring‐Opening Cyclization of Spirocyclopropanes with Stabilized Phosphorus Ylides: Access to Indane and Azulene Skeletons”, Adv Synth Catal, 365:15 (2023), 2536
D. A. Knyazev, M. A. Belaya, A. D. Volodin, A. A. Korlyukov, R. A. Novikov, Yu. V. Tomilov, “Gallium trichloride-mediated reactions of 'double' donor–acceptor cyclopropanes with alkenes and dienes”, Mendeleev Commun., 33:1 (2023), 30–33
Anna E. Vartanova, Irina I. Levina, Nina K. Ratmanova, Ivan A. Andreev, Olga A. Ivanova, Igor V. Trushkov, “Ambident reactivity of 5-aminopyrazoles towards donor–acceptor cyclopropanes”, Org. Biomol. Chem., 20:39 (2022), 7795
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