Novel upper rim functionalizations of calix[4]arenes using the Tscherniac-Einhorn amidomethylation reaction

K.J.C. Bommel; Folke Westerhof; Willem Verboom; David Reinhoudt; A.J.R.L. Hulst

doi:10.1002/(SICI)1521-3897(199904)341:3<284::AID-PRAC284>3.0.CO;2-7

Novel upper rim functionalizations of calix[4]arenes using the Tscherniac-Einhorn amidomethylation reaction

K.J.C. Bommel
, Folke Westerhof
, Willem Verboom
, David Reinhoudt
, A.J.R.L. Hulst

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

6 Citations (Scopus)

6 Downloads (Pure)

Abstract

A variety of novel upper rim functionalized calix-[4]arenes have been synthesized, using the Tscherniac-Einhorn amidomethylation reaction. Partially or fully alkylated calix [4]arenes bearing propyl or ethoxyethyl substituents could be easily condensed with various N-methylol-amides and -imides under mild conditions. The resulting methyl-acetamido- (4a, 4b, 7a), methylchloroacetamido (4c, 4d,7b, 7c,9 methylphthalimido (4e, 4f, 4h)and methylchloroacetamido methylphthalimido functionalized calix[4]arenes (5) were obtained in yields varying from 30 till 97%. The amidomethylation reactions were proven to be independent of the conformation of the calix[4]arene.

Original language	Undefined
Pages (from-to)	284-290
Journal	Journal für praktische Chemie
Volume	341
Issue number	341
DOIs	https://doi.org/10.1002/(SICI)1521-3897(199904)341:3<284::AID-PRAC284>3.0.CO;2-7
Publication status	Published - 1999

Keywords

METIS-105957
Calixarenes
IR-11026
Synthetic methods
electrophilic aromatic substitutions
amidomethylation
C-C coupling

Access to Document

10.1002/(SICI)1521-3897(199904)341:3<284::AID-PRAC284>3.0.CO;2-7

Cite this

@article{c45035211b5d465d90a33b0c83479538,

title = "Novel upper rim functionalizations of calix[4]arenes using the Tscherniac-Einhorn amidomethylation reaction",

abstract = "A variety of novel upper rim functionalized calix-[4]arenes have been synthesized, using the Tscherniac-Einhorn amidomethylation reaction. Partially or fully alkylated calix [4]arenes bearing propyl or ethoxyethyl substituents could be easily condensed with various N-methylol-amides and -imides under mild conditions. The resulting methyl-acetamido- (4a, 4b, 7a), methylchloroacetamido (4c, 4d,7b, 7c,9 methylphthalimido (4e, 4f, 4h)and methylchloroacetamido methylphthalimido functionalized calix[4]arenes (5) were obtained in yields varying from 30 till 97\%. The amidomethylation reactions were proven to be independent of the conformation of the calix[4]arene.",

keywords = "METIS-105957, Calixarenes, IR-11026, Synthetic methods, electrophilic aromatic substitutions, amidomethylation, C-C coupling",

author = "K.J.C. Bommel and Folke Westerhof and Willem Verboom and David Reinhoudt and A.J.R.L. Hulst",

year = "1999",

doi = "10.1002/(SICI)1521-3897(199904)341:3<284::AID-PRAC284>3.0.CO;2-7",

language = "Undefined",

volume = "341",

pages = "284--290",

journal = "Journal f{\"u}r praktische Chemie",

issn = "1436-9966",

publisher = "Wiley-VCH Verlag",

number = "341",

}

TY - JOUR

T1 - Novel upper rim functionalizations of calix[4]arenes using the Tscherniac-Einhorn amidomethylation reaction

AU - Bommel, K.J.C.

AU - Westerhof, Folke

AU - Verboom, Willem

AU - Reinhoudt, David

AU - Hulst, A.J.R.L.

PY - 1999

Y1 - 1999

N2 - A variety of novel upper rim functionalized calix-[4]arenes have been synthesized, using the Tscherniac-Einhorn amidomethylation reaction. Partially or fully alkylated calix [4]arenes bearing propyl or ethoxyethyl substituents could be easily condensed with various N-methylol-amides and -imides under mild conditions. The resulting methyl-acetamido- (4a, 4b, 7a), methylchloroacetamido (4c, 4d,7b, 7c,9 methylphthalimido (4e, 4f, 4h)and methylchloroacetamido methylphthalimido functionalized calix[4]arenes (5) were obtained in yields varying from 30 till 97%. The amidomethylation reactions were proven to be independent of the conformation of the calix[4]arene.

AB - A variety of novel upper rim functionalized calix-[4]arenes have been synthesized, using the Tscherniac-Einhorn amidomethylation reaction. Partially or fully alkylated calix [4]arenes bearing propyl or ethoxyethyl substituents could be easily condensed with various N-methylol-amides and -imides under mild conditions. The resulting methyl-acetamido- (4a, 4b, 7a), methylchloroacetamido (4c, 4d,7b, 7c,9 methylphthalimido (4e, 4f, 4h)and methylchloroacetamido methylphthalimido functionalized calix[4]arenes (5) were obtained in yields varying from 30 till 97%. The amidomethylation reactions were proven to be independent of the conformation of the calix[4]arene.

KW - METIS-105957

KW - Calixarenes

KW - IR-11026

KW - Synthetic methods

KW - electrophilic aromatic substitutions

KW - amidomethylation

KW - C-C coupling

U2 - 10.1002/(SICI)1521-3897(199904)341:3<284::AID-PRAC284>3.0.CO;2-7

DO - 10.1002/(SICI)1521-3897(199904)341:3<284::AID-PRAC284>3.0.CO;2-7

M3 - Article

SN - 1436-9966

VL - 341

SP - 284

EP - 290

JO - Journal für praktische Chemie

JF - Journal für praktische Chemie

IS - 341

ER -