One-Step Synthesis of C2v-Symmetric Resorcin[4]arene Tetraethers

Jordan N. Smith; Thomasin K. Brind; Simon B. Petrie; Mikaela S. Grant; Nigel T. Lucas

doi:10.1021/acs.joc.0c00128

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

Jordan N. Smith, Thomasin K. Brind, Simon B. Petrie, Mikaela S. Grant, Nigel T. Lucas^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4574-4580
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	85
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.0c00128
Publication status	Published - 20 Mar 2020
Externally published	Yes

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title = "One-Step Synthesis of C2v-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 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.",

author = "Smith, {Jordan N.} and Brind, {Thomasin K.} and Petrie, {Simon B.} and Grant, {Mikaela S.} and Lucas, {Nigel T.}",

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doi = "10.1021/acs.joc.0c00128",

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AU - Smith, Jordan N.

AU - Brind, Thomasin K.

AU - Petrie, Simon B.

AU - Grant, Mikaela S.

AU - Lucas, Nigel T.

PY - 2020/3/20

Y1 - 2020/3/20

N2 - 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.

AB - 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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SN - 0022-3263

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SP - 4574

EP - 4580

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

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

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