Capping the upper and lower rims of calix[4]arenes by aryl dinitrile oxide reactions

Ya Jiun Shiao; Pei Chen Chiang; Annamalai Senthilvelan; Ming Tsung Tsai; Gene Hsiang Lee; Wen-Sheng Chung

doi:10.1016/j.tetlet.2006.09.070

Capping the upper and lower rims of calix[4]arenes by aryl dinitrile oxide reactions

Ya Jiun Shiao, Pei Chen Chiang, Annamalai Senthilvelan, Ming Tsung Tsai, Gene Hsiang Lee, Wen-Sheng Chung^*

^*Corresponding author for this work

Department of Applied Chemistry

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

20 Scopus citations

Abstract

1,3-Dipolar cycloadditions of upper- and lower-rim diallylcalix[4]arenes (1 and 3) with aryl dinitrile oxides provide a unique and efficient way of capping the calix[4]arenes. When dinitrile oxides reacted with 5-allylcalix[4]arene 7, they underwent a 1,3-dipolar cycloaddition on one side and an electrophilic substitution on the other side, which led to a novel type of asymmetric calix[4]arenes (9 and 12).

Original language	English
Pages (from-to)	8383-8386
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2006.09.070
State	Published - 20 Nov 2006

Keywords

1,3-Dipolar cycloaddition
Asymmetric calix[4]arenes
Electrophilic substitution
Isoxazolines

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title = "Capping the upper and lower rims of calix[4]arenes by aryl dinitrile oxide reactions",

abstract = "1,3-Dipolar cycloadditions of upper- and lower-rim diallylcalix[4]arenes (1 and 3) with aryl dinitrile oxides provide a unique and efficient way of capping the calix[4]arenes. When dinitrile oxides reacted with 5-allylcalix[4]arene 7, they underwent a 1,3-dipolar cycloaddition on one side and an electrophilic substitution on the other side, which led to a novel type of asymmetric calix[4]arenes (9 and 12).",

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T1 - Capping the upper and lower rims of calix[4]arenes by aryl dinitrile oxide reactions

AU - Shiao, Ya Jiun

AU - Chiang, Pei Chen

AU - Senthilvelan, Annamalai

AU - Tsai, Ming Tsung

AU - Lee, Gene Hsiang

AU - Chung, Wen-Sheng

PY - 2006/11/20

Y1 - 2006/11/20

N2 - 1,3-Dipolar cycloadditions of upper- and lower-rim diallylcalix[4]arenes (1 and 3) with aryl dinitrile oxides provide a unique and efficient way of capping the calix[4]arenes. When dinitrile oxides reacted with 5-allylcalix[4]arene 7, they underwent a 1,3-dipolar cycloaddition on one side and an electrophilic substitution on the other side, which led to a novel type of asymmetric calix[4]arenes (9 and 12).

AB - 1,3-Dipolar cycloadditions of upper- and lower-rim diallylcalix[4]arenes (1 and 3) with aryl dinitrile oxides provide a unique and efficient way of capping the calix[4]arenes. When dinitrile oxides reacted with 5-allylcalix[4]arene 7, they underwent a 1,3-dipolar cycloaddition on one side and an electrophilic substitution on the other side, which led to a novel type of asymmetric calix[4]arenes (9 and 12).

KW - 1,3-Dipolar cycloaddition

KW - Asymmetric calix[4]arenes

KW - Electrophilic substitution

KW - Isoxazolines

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DO - 10.1016/j.tetlet.2006.09.070

M3 - Article

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VL - 47

SP - 8383

EP - 8386

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 47

ER -

Capping the upper and lower rims of calix[4]arenes by aryl dinitrile oxide reactions

Abstract

Keywords

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