Selective functionalization of calix[4]arenes via tricarbonylchromium complexes

Taketoshi Kikuchi, Hideshi Iki, Hirohisa Tsuzuki, Seiji Shinkai

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Tricarbonylchromium complexes of 25,26,27,28-tetrapropoxycalix-[4]arene conformers (l4Pr) were synthesized. Since the benzene ring is activated through complexation with Cr(CO)3, the functional groups (e.g. —D, —CH3, and —CHO) could be selectively introduced into the Cr(CO)3-complexed benzene ring. The substitution reaction occurred mainly at the p-position. The para selectivity was attributed to the steric crowding being relatively lower than that around the meta and benzyl position. This view was supported by the X-ray crystallographic study of 1,3-alternate-l4Pr. (CO)3. This is a novel and general methodology for selective introduction of functional groups into calix[n]arenes.

Original languageEnglish
Pages (from-to)103-106
Number of pages4
JournalSupramolecular Chemistry
Volume1
Issue number2
DOIs
Publication statusPublished - Jan 1 1993

Fingerprint

Carbon Monoxide
Benzene
Functional groups
Calixarenes
Complexation
Substitution reactions
X rays

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Selective functionalization of calix[4]arenes via tricarbonylchromium complexes. / Kikuchi, Taketoshi; Iki, Hideshi; Tsuzuki, Hirohisa; Shinkai, Seiji.

In: Supramolecular Chemistry, Vol. 1, No. 2, 01.01.1993, p. 103-106.

Research output: Contribution to journalArticle

Kikuchi, Taketoshi ; Iki, Hideshi ; Tsuzuki, Hirohisa ; Shinkai, Seiji. / Selective functionalization of calix[4]arenes via tricarbonylchromium complexes. In: Supramolecular Chemistry. 1993 ; Vol. 1, No. 2. pp. 103-106.
@article{18ba8b61929643e1b7cfa7e0dadeefcc,
title = "Selective functionalization of calix[4]arenes via tricarbonylchromium complexes",
abstract = "Tricarbonylchromium complexes of 25,26,27,28-tetrapropoxycalix-[4]arene conformers (l4Pr) were synthesized. Since the benzene ring is activated through complexation with Cr(CO)3, the functional groups (e.g. —D, —CH3, and —CHO) could be selectively introduced into the Cr(CO)3-complexed benzene ring. The substitution reaction occurred mainly at the p-position. The para selectivity was attributed to the steric crowding being relatively lower than that around the meta and benzyl position. This view was supported by the X-ray crystallographic study of 1,3-alternate-l4Pr. (CO)3. This is a novel and general methodology for selective introduction of functional groups into calix[n]arenes.",
author = "Taketoshi Kikuchi and Hideshi Iki and Hirohisa Tsuzuki and Seiji Shinkai",
year = "1993",
month = "1",
day = "1",
doi = "10.1080/10610279308040654",
language = "English",
volume = "1",
pages = "103--106",
journal = "Supramolecular Chemistry",
issn = "1061-0278",
publisher = "Taylor and Francis Ltd.",
number = "2",

}

TY - JOUR

T1 - Selective functionalization of calix[4]arenes via tricarbonylchromium complexes

AU - Kikuchi, Taketoshi

AU - Iki, Hideshi

AU - Tsuzuki, Hirohisa

AU - Shinkai, Seiji

PY - 1993/1/1

Y1 - 1993/1/1

N2 - Tricarbonylchromium complexes of 25,26,27,28-tetrapropoxycalix-[4]arene conformers (l4Pr) were synthesized. Since the benzene ring is activated through complexation with Cr(CO)3, the functional groups (e.g. —D, —CH3, and —CHO) could be selectively introduced into the Cr(CO)3-complexed benzene ring. The substitution reaction occurred mainly at the p-position. The para selectivity was attributed to the steric crowding being relatively lower than that around the meta and benzyl position. This view was supported by the X-ray crystallographic study of 1,3-alternate-l4Pr. (CO)3. This is a novel and general methodology for selective introduction of functional groups into calix[n]arenes.

AB - Tricarbonylchromium complexes of 25,26,27,28-tetrapropoxycalix-[4]arene conformers (l4Pr) were synthesized. Since the benzene ring is activated through complexation with Cr(CO)3, the functional groups (e.g. —D, —CH3, and —CHO) could be selectively introduced into the Cr(CO)3-complexed benzene ring. The substitution reaction occurred mainly at the p-position. The para selectivity was attributed to the steric crowding being relatively lower than that around the meta and benzyl position. This view was supported by the X-ray crystallographic study of 1,3-alternate-l4Pr. (CO)3. This is a novel and general methodology for selective introduction of functional groups into calix[n]arenes.

UR - http://www.scopus.com/inward/record.url?scp=0001534323&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001534323&partnerID=8YFLogxK

U2 - 10.1080/10610279308040654

DO - 10.1080/10610279308040654

M3 - Article

VL - 1

SP - 103

EP - 106

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

SN - 1061-0278

IS - 2

ER -