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Pathways of Pd-catalyzed cyclopropanation of tetrahydroindene with diazomethane

Evgenii Vladimirovich Shulishov 1
Evgenii Vladimirovich Shulishov
, 
Olga Aleksandrovna Pantyukh 1
Olga Aleksandrovna Pantyukh
, 
Leonid Gennad'evich Menchikov 1
Leonid Gennad'evich Menchikov
, 
10.1016/j.mencom.2020.09.020
Published 2020-08-31
Communication , Volume 30, Issue 5, 612-614
4
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Shulishov E. V. et al. Pathways of Pd-catalyzed cyclopropanation of tetrahydroindene with diazomethane // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 612-614.
GOST all authors (up to 50) Copy
Shulishov E. V., Pantyukh O. A., Menchikov L. G., Tomilov Y. V. Pathways of Pd-catalyzed cyclopropanation of tetrahydroindene with diazomethane // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 612-614.
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TY - JOUR
DO - 10.1016/j.mencom.2020.09.020
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.020
TI - Pathways of Pd-catalyzed cyclopropanation of tetrahydroindene with diazomethane
T2 - Mendeleev Communications
AU - Shulishov, Evgenii Vladimirovich
AU - Pantyukh, Olga Aleksandrovna
AU - Menchikov, Leonid Gennad'evich
AU - Tomilov, Yury Vasil'evich
PY - 2020
DA - 2020/08/31
PB - Mendeleev Communications
SP - 612-614
IS - 5
VL - 30
ER -
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@article{2020_Shulishov,
author = {Evgenii Vladimirovich Shulishov and Olga Aleksandrovna Pantyukh and Leonid Gennad'evich Menchikov and Yury Vasil'evich Tomilov},
title = {Pathways of Pd-catalyzed cyclopropanation of tetrahydroindene with diazomethane},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.020},
number = {5},
pages = {612--614},
doi = {10.1016/j.mencom.2020.09.020}
}
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Cite this
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Shulishov, Evgenii Vladimirovich, et al. “Pathways of Pd-catalyzed cyclopropanation of tetrahydroindene with diazomethane.” Mendeleev Communications, vol. 30, no. 5, Aug. 2020, pp. 612-614. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.020.

Keywords

N-methyl-N-nitrosourea
3a,4,7,7a-tetrahydro-1H-indene
cyclopropanation
diazomethane
palladium catalysis

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.

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