Synthesis and Physicochemical Properties of Functionalized <i>cis–</i> 2‐((Fluoro)Alkyl)Cyclobutanes
Efficient decagram-scale synthesis of (fluoro)alkyl-containing cis-1,2-disubstituted cyclobutane-derived building blocks is described. Starting from commercially available chemicals, target cyclobutylamines, carboxylic acids, and other valuable derivatives are obtained in 3-8 steps on up to a 39 g scale. Physicochemical characterization of the prepared compounds and their model derivatives reveal the distinct features of cis-1,2-disubstituted cyclobutanes (namely, significantly lowered lipophilicity) as compared to their previously reported trans-isomeric counterparts. Computational analysis, along with experimentally obtained structural properties, suggest the decisive influence of the compounds' conformation on the discussed properties.
Authors
- Oleksandr S. Liashuk (ORCID: https://orcid.org/0000-0002-2677-435X)
- Oleksandr O. Grygorenko (ORCID: https://orcid.org/0000-0002-6036-5859)
- Sergey V. Ryabukhin (ORCID: https://orcid.org/0000-0003-4281-8268)
- Anton V. Chernykh (ORCID: https://orcid.org/0000-0002-2292-4138)
- Dmitriy M. Volochnyuk (ORCID: https://orcid.org/0000-0001-6519-1467)
- Andrii V. Kozytskyi
- Oleksandr S. Olifir
- Svitlana V. Shishkina (ORCID: https://orcid.org/0000-0002-3946-1061)
- Petro Borysko (ORCID: https://orcid.org/0000-0002-5840-5233)
- Dmytro Lesyk (ORCID: https://orcid.org/0009-0001-3391-5165)
- Kyrylo O. Kononenko
- Artem Y. Michuda
- Karina Turenko
Institutions
- National Academy of Sciences of Ukraine (UA)
- Taras Shevchenko National University of Kyiv (UA)
- State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine (UA)
- Institute of Bioorganic Chemistry and Petrochemistry V.P. Kukhar (UA)
- Institute of Organic Chemistry (UA)
- Enamine (Ukraine) (UA)
Publication Details
- Journal
- ChemPlusChem
- Published
- 2025-06-16
- DOI
- https://doi.org/10.1002/cplu.202500150
- Citations
- 6
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 4.74
Funders
- Ministry of Education and Science of Ukraine
- Enamine