Preparation and Crystal Structure of the 1,3-alternate Atropisomer of a Calix[4]radialene

Norbert Itzhak; Silvio E. Biali

doi:10.1002/ejoc.201500319

Preparation and Crystal Structure of the 1,3-alternate Atropisomer of a Calix[4]radialene

Norbert Itzhak, Silvio E. Biali^*

^*Corresponding author for this work

Institute of Chemistry

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

6 Scopus citations

Abstract

Alkylation of the tetrahydroxy-tetraoxocalix[4]arene 5 with n-butyl bromide proceeds in a stereoselective fashion and affords exclusively a single atropisomer of the tetraoxocalix[4]arene tetrabutyl ether derivative. Reaction with MeLi followed by fourfold acid-catalyzed elimination of water affords the rigid calix[4]radialene 8. The crystal structure of 8 corroborated the proposed calixradialene structure and indicated an 1,3-alternate arrangement of the rings.

Original language	American English
Pages (from-to)	3221-3225
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	15
DOIs	https://doi.org/10.1002/ejoc.201500319
State	Published - May 2015

Bibliographical note

Funding Information:
This research was supported by the Israel Science Foundation (grant No. 223/14). We thank Dr. Benny Bogoslavsky for the crystal-structure determination.

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Calixarenes
Cyclophanes
Macrocycles
Nucleophilic substitution
Stereochemistry

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10.1002/ejoc.201500319

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title = "Preparation and Crystal Structure of the 1,3-alternate Atropisomer of a Calix[4]radialene",

abstract = "Alkylation of the tetrahydroxy-tetraoxocalix[4]arene 5 with n-butyl bromide proceeds in a stereoselective fashion and affords exclusively a single atropisomer of the tetraoxocalix[4]arene tetrabutyl ether derivative. Reaction with MeLi followed by fourfold acid-catalyzed elimination of water affords the rigid calix[4]radialene 8. The crystal structure of 8 corroborated the proposed calixradialene structure and indicated an 1,3-alternate arrangement of the rings.",

keywords = "Calixarenes, Cyclophanes, Macrocycles, Nucleophilic substitution, Stereochemistry",

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

note = "Funding Information: This research was supported by the Israel Science Foundation (grant No. 223/14). We thank Dr. Benny Bogoslavsky for the crystal-structure determination. Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2015",

month = may,

doi = "10.1002/ejoc.201500319",

language = "American English",

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pages = "3221--3225",

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T1 - Preparation and Crystal Structure of the 1,3-alternate Atropisomer of a Calix[4]radialene

AU - Itzhak, Norbert

AU - Biali, Silvio E.

N1 - Funding Information: This research was supported by the Israel Science Foundation (grant No. 223/14). We thank Dr. Benny Bogoslavsky for the crystal-structure determination. Publisher Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2015/5

Y1 - 2015/5

N2 - Alkylation of the tetrahydroxy-tetraoxocalix[4]arene 5 with n-butyl bromide proceeds in a stereoselective fashion and affords exclusively a single atropisomer of the tetraoxocalix[4]arene tetrabutyl ether derivative. Reaction with MeLi followed by fourfold acid-catalyzed elimination of water affords the rigid calix[4]radialene 8. The crystal structure of 8 corroborated the proposed calixradialene structure and indicated an 1,3-alternate arrangement of the rings.

AB - Alkylation of the tetrahydroxy-tetraoxocalix[4]arene 5 with n-butyl bromide proceeds in a stereoselective fashion and affords exclusively a single atropisomer of the tetraoxocalix[4]arene tetrabutyl ether derivative. Reaction with MeLi followed by fourfold acid-catalyzed elimination of water affords the rigid calix[4]radialene 8. The crystal structure of 8 corroborated the proposed calixradialene structure and indicated an 1,3-alternate arrangement of the rings.

KW - Calixarenes

KW - Cyclophanes

KW - Macrocycles

KW - Nucleophilic substitution

KW - Stereochemistry

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DO - 10.1002/ejoc.201500319

M3 - Article

AN - SCOPUS:85027920743

SN - 1434-193X

VL - 2015

SP - 3221

EP - 3225

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 15

ER -

Preparation and Crystal Structure of the 1,3-alternate Atropisomer of a Calix[4]radialene

Abstract

Bibliographical note

Keywords

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