Synthesis and characterization of the O-alkylation products of resorcinarene

K. Salorinne, E. Nauha, M. Nissinen, Jarmo Ropponen (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

8 Citations (Scopus)

Abstract

O‐Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of partially O‐alkylated resorcinarene derivatives with terminal alkyne functionality. The degree of alkylation was affected by the reactivity of the alkylating halide used. NMR spectroscopy proved to be an ideal tool for analyzing the complex reaction mixtures and the isolated products based on the symmetry and degree of alkylation of the resorcinarene derivatives. Single‐crystal X‐ray diffraction studies furthermore showed diversity in the self‐assembly of the various O‐alkylation products that was greatly affected by the degree of alkylation, as well as the nature of the alkyne moiety.
Original languageEnglish
Pages (from-to)1591-1598
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number8
DOIs
Publication statusPublished - 2013
MoE publication typeA1 Journal article-refereed

Fingerprint

alkylation
Alkylation
Alkynes
alkynes
halides
synthesis
products
Derivatives
Nuclear magnetic resonance spectroscopy
reactivity
Diffraction
nuclear magnetic resonance
symmetry
diffraction
spectroscopy
resorcinarene

Cite this

@article{bf414270af6b430da5f8ba232192f33b,
title = "Synthesis and characterization of the O-alkylation products of resorcinarene",
abstract = "O‐Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of partially O‐alkylated resorcinarene derivatives with terminal alkyne functionality. The degree of alkylation was affected by the reactivity of the alkylating halide used. NMR spectroscopy proved to be an ideal tool for analyzing the complex reaction mixtures and the isolated products based on the symmetry and degree of alkylation of the resorcinarene derivatives. Single‐crystal X‐ray diffraction studies furthermore showed diversity in the self‐assembly of the various O‐alkylation products that was greatly affected by the degree of alkylation, as well as the nature of the alkyne moiety.",
author = "K. Salorinne and E. Nauha and M. Nissinen and Jarmo Ropponen",
year = "2013",
doi = "10.1002/ejoc.201201509",
language = "English",
pages = "1591--1598",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "8",

}

Synthesis and characterization of the O-alkylation products of resorcinarene. / Salorinne, K.; Nauha, E.; Nissinen, M.; Ropponen, Jarmo (Corresponding Author).

In: European Journal of Organic Chemistry, No. 8, 2013, p. 1591-1598.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Synthesis and characterization of the O-alkylation products of resorcinarene

AU - Salorinne, K.

AU - Nauha, E.

AU - Nissinen, M.

AU - Ropponen, Jarmo

PY - 2013

Y1 - 2013

N2 - O‐Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of partially O‐alkylated resorcinarene derivatives with terminal alkyne functionality. The degree of alkylation was affected by the reactivity of the alkylating halide used. NMR spectroscopy proved to be an ideal tool for analyzing the complex reaction mixtures and the isolated products based on the symmetry and degree of alkylation of the resorcinarene derivatives. Single‐crystal X‐ray diffraction studies furthermore showed diversity in the self‐assembly of the various O‐alkylation products that was greatly affected by the degree of alkylation, as well as the nature of the alkyne moiety.

AB - O‐Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of partially O‐alkylated resorcinarene derivatives with terminal alkyne functionality. The degree of alkylation was affected by the reactivity of the alkylating halide used. NMR spectroscopy proved to be an ideal tool for analyzing the complex reaction mixtures and the isolated products based on the symmetry and degree of alkylation of the resorcinarene derivatives. Single‐crystal X‐ray diffraction studies furthermore showed diversity in the self‐assembly of the various O‐alkylation products that was greatly affected by the degree of alkylation, as well as the nature of the alkyne moiety.

U2 - 10.1002/ejoc.201201509

DO - 10.1002/ejoc.201201509

M3 - Article

SP - 1591

EP - 1598

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 8

ER -