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

7 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.\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = mar,

day = "20",

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

language = "English",

volume = "85",

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journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - One-Step Synthesis of C2v-Symmetric Resorcin[4]arene Tetraethers

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.

UR - https://www.scopus.com/pages/publications/85081218559

U2 - 10.1021/acs.joc.0c00128

DO - 10.1021/acs.joc.0c00128

M3 - Article

C2 - 32125153

AN - SCOPUS:85081218559

SN - 0022-3263

VL - 85

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

Abstract

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