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Moving of the tetramethylbutanediyl substituent over the catecholcarbaldehyde core

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10.71267/mencom.7838
Published 2025-11-29
Communication , Volume 36, Issue 1, 117-119
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Zherebtsov M. A. et al. Moving of the tetramethylbutanediyl substituent over the catecholcarbaldehyde core // Mendeleev Communications. 2025. Vol. 36. No. 1. pp. 117-119.
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Zherebtsov M. A., Anisimova N. D., Tarakanova A. E., Arsenyev M. V., Chesnokov S. A. Moving of the tetramethylbutanediyl substituent over the catecholcarbaldehyde core // Mendeleev Communications. 2025. Vol. 36. No. 1. pp. 117-119.
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TY - JOUR
DO - 10.71267/mencom.7838
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7838
TI - Moving of the tetramethylbutanediyl substituent over the catecholcarbaldehyde core
T2 - Mendeleev Communications
AU - Zherebtsov, Maxim Aleksandrovich
AU - Anisimova, Natalia D.
AU - Tarakanova, Anastasiya E
AU - Arsenyev, Maxim Vyacheslavovich
AU - Chesnokov, Sergey Arturovich
PY - 2025
DA - 2025/11/29
PB - Mendeleev Communications
SP - 117-119
IS - 1
VL - 36
ER -
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@article{2025_Zherebtsov,
author = {Maxim Aleksandrovich Zherebtsov and Natalia D. Anisimova and Anastasiya E Tarakanova and Maxim Vyacheslavovich Arsenyev and Sergey Arturovich Chesnokov},
title = {Moving of the tetramethylbutanediyl substituent over the catecholcarbaldehyde core},
journal = {Mendeleev Communications},
year = {2025},
volume = {36},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7838},
number = {1},
pages = {117--119},
doi = {10.71267/mencom.7838}
}
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Zherebtsov, Maxim Aleksandrovich, et al. “Moving of the tetramethylbutanediyl substituent over the catecholcarbaldehyde core.” Mendeleev Communications, vol. 36, no. 1, Nov. 2025, pp. 117-119. https://mendcomm.colab.ws/publications/10.71267/mencom.7838.
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Keywords

alkylation
catecholcarbaldehyde
catechols
o-quinones
oxidation
reduction.

Abstract

1,1,4,4-Tetramethylbutane-1,4-diyl substituent fused to positions 5,6 of 2,3-dihydroxybezaldehyde (‘catecholcarbaldehyde’) upon the action of acids readily moves to positions 3,4 to afford less strained isomer, with the optimum reagent being neat methanesulfonic acid acting at room temperature. The same compound was prepared in four steps from 3,4-(1,1,4,4-tetramethylbutane-1,4-diyl)phenol; the intermediates were the mixtures of 3,4- and 4,5-fused o-benzoquinones/catechols whereas the last step involved the abovementioned substituent moving.

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