Байланысты: Сборник конф Фараби Әлемі 2023 химфак-печать
EFFICIENT AND METAL-FREE SYNTHESIS OF M-ARYLOXY PHENOLS VIA A THREE-STEP PROCESS Amankulova D. Supervisor: Candidate of chemical sci., associate prof. Dyusebaeva M.А. Al-Farabi Kazakh National University Amankulova.dynara@mail.ru The synthesis of m-aryloxy phenols is an important area of research due to their diverse
applications in areas such as materials science and pharmaceuticals. However, the strong influence
of the hydroxyl group on the ortho/para substitution of the aromatic ring can pose a significant
challenge in the synthesis of meta-substituted phenol derivatives. Therefore, there is a pressing need
for the development of novel synthetic methods that can avoid the influence of the hydroxyl group
and enable the synthesis of a wider range of m-aryloxy phenols with enhanced properties.
We have developed a synthetic strategy to address the challenge of synthesizing m-aryloxy
phenols. The method involves using 3-chlorocyclohex-2-en-1-one and suitable phenol derivatives in
a three-step process. This approach has allowed for the preparation of 17 (6 of them are previously
not described) final compounds with good to excellent yields, demonstrating the effectiveness of
the synthetic strategy in generating a range of m-aryloxy phenols. TLC was used to confirm
complete conversion of reactants, while the structural analysis of resulting compounds was
conducted using spectral techniques, such as IR, NMR, MS, and UV-Vis spectroscopy.
Our novel synthesis method for generating m-aryloxy phenols without the use of heavy
metals or ligands. The current method operates at ambient temperature, and avoids the procedural
steps typically required to overcome the o, p - directing effect of oxygen. This is achieved by taking
advantage of the readily available 1,3-functional group relationship inherent in the starting material,
cyclohexane-1,3-dione. The use of this new synthesis method eliminates the need for multiple
reagents and conditions typically required in multi-step reaction sequences.
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