The nucleophilic substitution route. A facile method for the fourfold functionalization of the methylene bridges of calix[4]arene

Ishay Columbus; Silvio E. Biali

doi:10.1021/ol0713178

The nucleophilic substitution route. A facile method for the fourfold functionalization of the methylene bridges of calix[4]arene

Ishay Columbus, Silvio E. Biali^*

^*Corresponding author for this work

Institute of Chemistry

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

38 Scopus citations

Abstract

The radical bromination of p-tert-butylcalixarene tetramethyl ether was reinvestigated and the product (2b) characterized by X-ray crystallography. The tetrabromo calixarene derivatives 2a or 2b react with alcohols (TFE, EtOH), azide, and 2-methylfuran under solvolytic conditions affording calixarene derivatives functionalized at the four bridges. The reaction with alcohols and the aromatic compound proceeds in stereoselective fashion and affords the rccc isomer of the tetrasubstituted product.

Original language	American English
Pages (from-to)	2927-2929
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	15
DOIs	https://doi.org/10.1021/ol0713178
State	Published - 19 Jul 2007

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title = "The nucleophilic substitution route. A facile method for the fourfold functionalization of the methylene bridges of calix[4]arene",

abstract = "The radical bromination of p-tert-butylcalixarene tetramethyl ether was reinvestigated and the product (2b) characterized by X-ray crystallography. The tetrabromo calixarene derivatives 2a or 2b react with alcohols (TFE, EtOH), azide, and 2-methylfuran under solvolytic conditions affording calixarene derivatives functionalized at the four bridges. The reaction with alcohols and the aromatic compound proceeds in stereoselective fashion and affords the rccc isomer of the tetrasubstituted product.",

author = "Ishay Columbus and Biali, {Silvio E.}",

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AU - Biali, Silvio E.

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N2 - The radical bromination of p-tert-butylcalixarene tetramethyl ether was reinvestigated and the product (2b) characterized by X-ray crystallography. The tetrabromo calixarene derivatives 2a or 2b react with alcohols (TFE, EtOH), azide, and 2-methylfuran under solvolytic conditions affording calixarene derivatives functionalized at the four bridges. The reaction with alcohols and the aromatic compound proceeds in stereoselective fashion and affords the rccc isomer of the tetrasubstituted product.

AB - The radical bromination of p-tert-butylcalixarene tetramethyl ether was reinvestigated and the product (2b) characterized by X-ray crystallography. The tetrabromo calixarene derivatives 2a or 2b react with alcohols (TFE, EtOH), azide, and 2-methylfuran under solvolytic conditions affording calixarene derivatives functionalized at the four bridges. The reaction with alcohols and the aromatic compound proceeds in stereoselective fashion and affords the rccc isomer of the tetrasubstituted product.

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JF - Organic Letters

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The nucleophilic substitution route. A facile method for the fourfold functionalization of the methylene bridges of calix[4]arene

Abstract

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