An Expedient Synthesis of Ketocalix[6]arene Hexamethyl Ether

Norbert Itzhak; Silvio E. Biali

doi:10.1055/s-0037-1609574

An Expedient Synthesis of Ketocalix[6]arene Hexamethyl Ether

Norbert Itzhak, Silvio E. Biali

Institute of Chemistry

The Hebrew University of Jerusalem

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

Abstract

p - tert -Butylcalix[6]arene hexamethyl ether was oxidized in one step to the corresponding ketocalix[6]arene via photochemical bromination (100 W spot lamp) with NBS in a chloroform/water mixture. A pentamethyl ketocalix[6]arene derivative was obtained by reaction of the ketocalix[6]arene hexamethyl ether with boron tribromide dimethyl sulfide complex, and characterized by X-ray crystallography. In the presence of base, the compound undergoes an intramolecular nucleophilic aromatic substitution reaction.

Original language	English
Pages (from-to)	3897-3901
Number of pages	5
Journal	Synthesis (Germany)
Volume	50
Issue number	19
DOIs	https://doi.org/10.1055/s-0037-1609574
State	Published - 5 Jul 2018

Keywords

bromine
calixarenes
cleavage
ether
oxidation
phenols

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1055/s-0037-1609574

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title = "An Expedient Synthesis of Ketocalix[6]arene Hexamethyl Ether",

abstract = "p - tert -Butylcalix[6]arene hexamethyl ether was oxidized in one step to the corresponding ketocalix[6]arene via photochemical bromination (100 W spot lamp) with NBS in a chloroform/water mixture. A pentamethyl ketocalix[6]arene derivative was obtained by reaction of the ketocalix[6]arene hexamethyl ether with boron tribromide dimethyl sulfide complex, and characterized by X-ray crystallography. In the presence of base, the compound undergoes an intramolecular nucleophilic aromatic substitution reaction.",

keywords = "bromine, calixarenes, cleavage, ether, oxidation, phenols",

author = "Norbert Itzhak and Biali, \{Silvio E.\}",

year = "2018",

month = jul,

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doi = "10.1055/s-0037-1609574",

language = "الإنجليزيّة",

volume = "50",

pages = "3897--3901",

journal = "Synthesis (Germany)",

issn = "0039-7881",

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TY - JOUR

T1 - An Expedient Synthesis of Ketocalix[6]arene Hexamethyl Ether

AU - Itzhak, Norbert

AU - Biali, Silvio E.

PY - 2018/7/5

Y1 - 2018/7/5

N2 - p - tert -Butylcalix[6]arene hexamethyl ether was oxidized in one step to the corresponding ketocalix[6]arene via photochemical bromination (100 W spot lamp) with NBS in a chloroform/water mixture. A pentamethyl ketocalix[6]arene derivative was obtained by reaction of the ketocalix[6]arene hexamethyl ether with boron tribromide dimethyl sulfide complex, and characterized by X-ray crystallography. In the presence of base, the compound undergoes an intramolecular nucleophilic aromatic substitution reaction.

AB - p - tert -Butylcalix[6]arene hexamethyl ether was oxidized in one step to the corresponding ketocalix[6]arene via photochemical bromination (100 W spot lamp) with NBS in a chloroform/water mixture. A pentamethyl ketocalix[6]arene derivative was obtained by reaction of the ketocalix[6]arene hexamethyl ether with boron tribromide dimethyl sulfide complex, and characterized by X-ray crystallography. In the presence of base, the compound undergoes an intramolecular nucleophilic aromatic substitution reaction.

KW - bromine

KW - calixarenes

KW - cleavage

KW - ether

KW - oxidation

KW - phenols

UR - http://www.scopus.com/inward/record.url?scp=85049866448&partnerID=8YFLogxK

U2 - 10.1055/s-0037-1609574

DO - 10.1055/s-0037-1609574

M3 - مقالة

SN - 0039-7881

VL - 50

SP - 3897

EP - 3901

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 19

ER -

An Expedient Synthesis of Ketocalix[6]arene Hexamethyl Ether

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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