One-Step Synthesis of C_2v-Symmetric Resorcin[4]arene Tetraethers

Abstract

The three-component reaction between a resorcinol, 1,3-dimethoxybenzene, and an alkyl aldehyde (R = C1–C11) along with BF3·OEt2 affords a C 2v-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.

Rigid, biconical hydrogen-bonded dimers that strongly encapsulate cationic guests in solution and the solid state

“…Cleavage of the eight exoannular methyl ethers of 1a with BBr 3 in CH 2 Cl 2 was facile; however, the product 2a was insoluble in the non-polar solvents CHCl 3 or CH 2 Cl 2 ( Scheme 1 ). To improve the solubility in non-polar solvents, we used our recent synthesis of C 2v -symmetric resorcin[4]arene derivatives 37 to prepare the undecyl analogue 1b in eight steps (see ESI † ).…”

Methodologies for the Derivatization of Resorcin[4]arenes at the Upper Rim ortho‐Positions

“…Recently, this approach was applied to the synthesis of distally functionalized resorcin[4]arene tetraethers (Scheme 15). [106] Herein, a reaction of a mixture of 1,3‐dimethoxybenzene, 2‐substituted resorcinols and aldehydes was performed in DCM in the presence of trifluoroboron diethyletherate. A number of 2‐substituted resorcinols were examined in the reaction including 2‐chlororesorcinol, 1,2,3‐trihydroxybenzene, 2‐bromoresorcinol and 2‐methylresorcinol.…”

Resorcin[4]arene‐based Cu(I) binuclear and mononuclear complexes as efficient catalysts for azide‐alkyne cycloaddition reactions

“…Their upper and lower rims could be modified by various substituents. [ 10–13 ] A series of resorcin[4]arene‐based derivatives have been synthesized, and this greatly enriched the structures and properties of their complexes. [ 14–19 ] However, there are few research about complexes constructed by resorcin[4]arenes and copper halides.…”