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Stereoisomerism in the representative tetracyclic dispiro ozonide derived from (methylene)dicyclohexanone with the 1,5-diketo arrangement

Taisia Ivanovna Akimova 1
Taisia Ivanovna Akimova
, 
Olga A Soldatkina 1
Olga A Soldatkina
, 
Vyacheslav G Savchenko 1
Vyacheslav G Savchenko
, 
Anna V Pilipenko 1
Anna V Pilipenko
, 
Alevtina A Kapustina 1
Alevtina A Kapustina
10.1016/j.mencom.2022.03.040
Published 2022-03-06
Communication , Volume 32, Issue 2, 271-273
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Akimova T. I. et al. Stereoisomerism in the representative tetracyclic dispiro ozonide derived from (methylene)dicyclohexanone with the 1,5-diketo arrangement // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 271-273.
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Akimova T. I., Soldatkina O. A., Savchenko V. G., Pilipenko A. V., Kapustina A. A. Stereoisomerism in the representative tetracyclic dispiro ozonide derived from (methylene)dicyclohexanone with the 1,5-diketo arrangement // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 271-273.
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TY - JOUR
DO - 10.1016/j.mencom.2022.03.040
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.040
TI - Stereoisomerism in the representative tetracyclic dispiro ozonide derived from (methylene)dicyclohexanone with the 1,5-diketo arrangement
T2 - Mendeleev Communications
AU - Akimova, Taisia Ivanovna
AU - Soldatkina, Olga A
AU - Savchenko, Vyacheslav G
AU - Pilipenko, Anna V
AU - Kapustina, Alevtina A
PY - 2022
DA - 2022/03/06
PB - Mendeleev Communications
SP - 271-273
IS - 2
VL - 32
ER -
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@article{2022_Akimova,
author = {Taisia Ivanovna Akimova and Olga A Soldatkina and Vyacheslav G Savchenko and Anna V Pilipenko and Alevtina A Kapustina},
title = {Stereoisomerism in the representative tetracyclic dispiro ozonide derived from (methylene)dicyclohexanone with the 1,5-diketo arrangement},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.040},
number = {2},
pages = {271--273},
doi = {10.1016/j.mencom.2022.03.040}
}
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Akimova, Taisia Ivanovna, et al. “Stereoisomerism in the representative tetracyclic dispiro ozonide derived from (methylene)dicyclohexanone with the 1,5-diketo arrangement.” Mendeleev Communications, vol. 32, no. 2, Mar. 2022, pp. 271-273. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.040.

Keywords

1,2,4-trioxolanes
1,5-diketones
dispiro compounds
hydrogen peroxide
ozonides
stereoisomerism
tetracyclic compounds

Abstract

The conditions and reasons for the stereoselective transformation of the rac form of 2,2′-(methylene)-dicyclohexanone into the meso- or rac-diastereomer of tetracyclic dispiro ozonide (1,2,4-trioxolane) in the reaction with 30% aqueous H2O2 in the presence of acid have been determined. A mechanism for the stereoisomerization of ozonides was proposed, and the stereochemistry of diastereomeric ozonides was established by NMR data.

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