التفاصيل البيبلوغرافية
| العنوان: |
Adamantylated Calix[4]arenes Bearing CuAAC-Ready 2-Azidoethyl or Propargyl Functionalities. |
| المؤلفون: |
Gorbunov, Alexander, Malakhova, Maria, Bezzubov, Stanislav, Lentin, Ivan, Kovalev, Vladimir, Vatsouro, Ivan |
| المصدر: |
Molbank; Jun2024, Vol. 2024 Issue 2, pM1821, 8p |
| مصطلحات موضوعية: |
AROMATIC compounds, PROPARGYL bromide, CALIXARENES, ADAMANTANE, X-ray diffraction, RESORCINARENES, ADAMANTANE derivatives |
| مستخلص: |
1,3-Alternate calix[4]arenes were prepared, having bulky adamantyl groups in the p-positions of all four aromatic units of the macrocycles and pairs of propargyl or 2-azidoethyl groups alternating with n-propyl groups at the phenol oxygen atoms. The step-wise syntheses were carried out through a selective distal alkylation of the parent p-adamantylcalix[4]arene with propargyl bromide or 1,2-dibromoethane, resulting in calix[4]arenes bearing pairs of propargyl or 2-bromoethyl groups at their narrow rims. The bromine atoms were replaced by azide groups, and then both calix[4]arene diethers were exhaustively alkylated at the remaining OH-groups with 1-iodopropane under stereoselective conditions to fix the macrocycles in an 1,3-alternate shape. The structures of the prepared p-adamantylcalix[4]arenes were confirmed by NMR and HRMS data, and, for the 1,3-alternate dipropargyl ether, the X-ray diffraction data were also collected. Preliminary data on the reactivity of the prepared calixarenes under the CuAAC conditions suggested a strong steric hampering created by the adamantane units nearby the reacting alkyne or azide groups that affected the outcome of the two-fold cycloaddition involving the calixarene bis(azides) or bis(alkynes) as complementary partners. [ABSTRACT FROM AUTHOR] |
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| قاعدة البيانات: |
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