| Title: |
Introduction of the Difluoro(methoxy)methyl Group into the Aromatic Ring and the Study of Its Electronic Properties. |
| Alternate Title: |
Введення дифторо(метокси)метильної групи в ароматичне кільце та дослідження її електронних властивостей. (Ukrainian) |
| Authors: |
Pashko, M. O.; Yagupolskii, Yu. L. |
| Source: |
Journal of Organic & Pharmaceutical Chemistry / Zhurnal Organichnoi ta Farmatsevtichnoi Khimii; 2024, Vol. 22 Issue 4, p10-16, 7p |
| Subject Terms: |
METHYL groups; GROUP rings; AROMATIC compounds; RESONANCE; MOLECULES |
| Abstract: |
A simple and efficient method for synthesizing aromatic compounds with a difluoro(methoxy)methyl fragment (CF2OCH3) by the fluorodesulfurization of thionoesters has been developed. Systematic screening identified SnCl4/DAST as the optimal reagent combination, providing excellent selectivity and high yields of target products. A series of aromatic difluoro(methoxy)methyl compounds was synthesized under these conditions. Further studies of the electronic properties of the difluoro(methoxy)-methyl group using 19F NMR allowed us to determine its Hammett constants for inductive (σI) and resonance (σR) effects. The results show that CF2OCH3 acts as a moderately electron-withdrawing substituent, underscoring its potential as a versatile group for designing organic molecules with precisely tuned electronic characteristics. [ABSTRACT FROM AUTHOR] |
| : |
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| Database: |
Complementary Index |