Abstract:
The Pd-catalyzed cyclopropanation of 3a,4,7,7a-tetrahydro-1H-indene with diazomethane unexpectedly affords monoand dicyclopropanation products in good yields, the cyclopentene double bond being approximately three times more reactive than the cyclohexene one. In contrast, similar independent competitive cyclopropanation of a cyclopentene–cyclohexene mixture has shown that cyclohexene exhibits an abnormally low reactivity differing by about two orders of magnitude.
Citation:
E. V. Shulishov, O. A. Pantyukh, L. G. Menchikov, Yu. V. Tomilov, “Pathways of Pd-catalyzed cyclopropanation of tetrahydroindene with diazomethane”, Mendeleev Commun., 30:5 (2020), 612–614
Linking options:
https://www.mathnet.ru/eng/mendc1269
https://www.mathnet.ru/eng/mendc/v30/i5/p612
This publication is cited in the following 4 articles:
Yuan Yao, Xinyue Zhang, Yingying Cao, Long Liu, Yanqiang Zhang, Suojiang Zhang, “Single-Site Pd Regulated by π-π Stacking for High-Selectivity Cyclopropanation Reaction”, J. Am. Chem. Soc., 146:45 (2024), 31053
Yury V. Tomilov, Anatoly I. Kazakov, Aleksander A. Molokanov, Olga A. Pantyukh, Evgeny V. Shulishov, Leonid G. Menchikov, Albina V. Nabatova, Tatyana S. Larikova, Natalya I. Varlamova, Leonid S. Yanovsky, “Thermochemical and physical characteristics of isomeric tetracycloundecanes obtained from endo- and exo-dicyclopentadienes”, Fuel, 373 (2024), 132294
Alexander V. Komkov, Leonid G. Menchikov, Andrey S. Dmitrenok, Natalya G. Kolotyrkina, Igor V. Zavarzin, “A method for the synthesis of spiro-1,3,4-thiadiazolines”, Chem Heterocycl Comp, 60:3-4 (2024), 183
L. G. Menchikov, E. V. Shulishov, Yu. V. Tomilov, “Recent advances in the catalytic cyclopropanation of unsaturated compounds with diazomethane”, Russian Chem. Reviews, 90:2 (2021), 199–230
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