Synthesis of 'macrocycle of macrocycles' containing 3 ~ 8 calix[4]arene units. Unexpected generation of large super-macrocycles

Pavel Lhoták, Masaru Kawaguchi, Atsushi Ikeda, Seiji Shinkai

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A new class of calixarene-based macrocycles consisting of three to eight calix[4]arene subunits has been prepared from starting 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dipropoxycalix[4]are ne. The macrocyclization has been achieved by direct alkylation with 1,6-dibromohexane in DMF in the presence of NaH or via appropriate intermediates. Thus, the starting compound was transformed into bis-calix[4]arenes bearing two bromoalkyl substituents or two hydroxyl groups in positions suitable for further cyclization. By the mutual reactions of the above noticed compounds supermacrocycles containing 3, 4, 6, and 8 calix[4]arene subunits connected by hexamethylene chains have been prepared and characterized. This is a novel strategy to design a 'macrocycle of macrocycles'.

Original languageEnglish
Pages (from-to)12399-12408
Number of pages10
JournalTetrahedron
Volume52
Issue number38
DOIs
Publication statusPublished - Sep 16 1996

Fingerprint

Bearings (structural)
Calixarenes
Cyclization
Alkylation
Hydroxyl Radical
calix(4)arene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis of 'macrocycle of macrocycles' containing 3 ~ 8 calix[4]arene units. Unexpected generation of large super-macrocycles. / Lhoták, Pavel; Kawaguchi, Masaru; Ikeda, Atsushi; Shinkai, Seiji.

In: Tetrahedron, Vol. 52, No. 38, 16.09.1996, p. 12399-12408.

Research output: Contribution to journalArticle

Lhoták, Pavel ; Kawaguchi, Masaru ; Ikeda, Atsushi ; Shinkai, Seiji. / Synthesis of 'macrocycle of macrocycles' containing 3 ~ 8 calix[4]arene units. Unexpected generation of large super-macrocycles. In: Tetrahedron. 1996 ; Vol. 52, No. 38. pp. 12399-12408.
@article{eaa2d33b8bd64d288c2b367de01c6151,
title = "Synthesis of 'macrocycle of macrocycles' containing 3 ~ 8 calix[4]arene units. Unexpected generation of large super-macrocycles",
abstract = "A new class of calixarene-based macrocycles consisting of three to eight calix[4]arene subunits has been prepared from starting 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dipropoxycalix[4]are ne. The macrocyclization has been achieved by direct alkylation with 1,6-dibromohexane in DMF in the presence of NaH or via appropriate intermediates. Thus, the starting compound was transformed into bis-calix[4]arenes bearing two bromoalkyl substituents or two hydroxyl groups in positions suitable for further cyclization. By the mutual reactions of the above noticed compounds supermacrocycles containing 3, 4, 6, and 8 calix[4]arene subunits connected by hexamethylene chains have been prepared and characterized. This is a novel strategy to design a 'macrocycle of macrocycles'.",
author = "Pavel Lhot{\'a}k and Masaru Kawaguchi and Atsushi Ikeda and Seiji Shinkai",
year = "1996",
month = "9",
day = "16",
doi = "10.1016/0040-4020(96)00738-7",
language = "English",
volume = "52",
pages = "12399--12408",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "38",

}

TY - JOUR

T1 - Synthesis of 'macrocycle of macrocycles' containing 3 ~ 8 calix[4]arene units. Unexpected generation of large super-macrocycles

AU - Lhoták, Pavel

AU - Kawaguchi, Masaru

AU - Ikeda, Atsushi

AU - Shinkai, Seiji

PY - 1996/9/16

Y1 - 1996/9/16

N2 - A new class of calixarene-based macrocycles consisting of three to eight calix[4]arene subunits has been prepared from starting 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dipropoxycalix[4]are ne. The macrocyclization has been achieved by direct alkylation with 1,6-dibromohexane in DMF in the presence of NaH or via appropriate intermediates. Thus, the starting compound was transformed into bis-calix[4]arenes bearing two bromoalkyl substituents or two hydroxyl groups in positions suitable for further cyclization. By the mutual reactions of the above noticed compounds supermacrocycles containing 3, 4, 6, and 8 calix[4]arene subunits connected by hexamethylene chains have been prepared and characterized. This is a novel strategy to design a 'macrocycle of macrocycles'.

AB - A new class of calixarene-based macrocycles consisting of three to eight calix[4]arene subunits has been prepared from starting 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dipropoxycalix[4]are ne. The macrocyclization has been achieved by direct alkylation with 1,6-dibromohexane in DMF in the presence of NaH or via appropriate intermediates. Thus, the starting compound was transformed into bis-calix[4]arenes bearing two bromoalkyl substituents or two hydroxyl groups in positions suitable for further cyclization. By the mutual reactions of the above noticed compounds supermacrocycles containing 3, 4, 6, and 8 calix[4]arene subunits connected by hexamethylene chains have been prepared and characterized. This is a novel strategy to design a 'macrocycle of macrocycles'.

UR - http://www.scopus.com/inward/record.url?scp=0030590473&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030590473&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(96)00738-7

DO - 10.1016/0040-4020(96)00738-7

M3 - Article

VL - 52

SP - 12399

EP - 12408

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 38

ER -