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Terminal Epoxides Functionalization. Tetraethylammonium Iodide-Catalyzed Meinwald Rearrangement and Synthesis of 1,3-Dioxolan
- Authors: Kharaneko A.O1, Kharaneko O.I2
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Affiliations:
- Research Institute of Physical and Organic Chemistry, Southern Federal University
- Litvinenko Institute of Physical Organic and Coal Chemistry
- Issue: Vol 61, No 11 (2025)
- Pages: 1585–1592
- Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
- URL: https://journals.rcsi.science/0514-7492/article/view/381755
- DOI: https://doi.org/10.7868/S3034630425110078
- ID: 381755
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Abstract
A new catalyst for Meinwald rearrangement and synthesis of 1,3-dioxolan is proposed for reactions of terminal epoxides as an example. A highly efficient and selective rearrangement in the presence of catalytic quantities of tetraethylammonium iodide was shown. Excellent yields of acetyl derivatives were obtained at this rearrangement. An anomalous condensation of 4-(3,6-dichloro-9H-carbazol-9-yl)-3-hydroxybutanenitrile with aldehydes and ketones was discovered. This condensation is accompanied by the elimination of water in an alkaline solution and only derivatives of Z-butadienes are formed.
About the authors
A. O Kharaneko
Research Institute of Physical and Organic Chemistry, Southern Federal University
Email: antonhar08@rambler.ru
ORCID iD: 0000-0002-8677-2647
Rostov-on-Don, Russia
O. I Kharaneko
Litvinenko Institute of Physical Organic and Coal Chemistry
ORCID iD: 0000-0003-1105-8227
Donetsk, Russia
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