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One-Step Synthesis of C2v-Symmetric Resorcin[4]arene Tetraethers
Jordan N Smith1, Thomasin K Brind1, Simon B Petrie1
1MacDiarmid Institute for Advanced Materials and Nanotechnology, Department of Chemistry, University of Otago, Union Place, Dunedin 9016, New Zealand.
Abstract:
The three-component reaction between a resorcinol, 1,3-dimethoxybenzene, and an alkyl aldehyde (R = C1-C11) along with BF3·OEt2 affords a C2v-symmetric resorcin[4]arene tetraether in one step; in most cases, the single isomer can be precipitated from the reaction mixture in moderate to excellent yields (up to 89%). The reaction is tolerant of 2-substituted resorcinols (R' = OH, Cl, Br, Me), allowing a third type of functionality to be regioselectively incorporated during the macrocyclization.
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