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 language | English |
|---|---|
| Pages (from-to) | 12399-12408 |
| Number of pages | 10 |
| Journal | Tetrahedron |
| Volume | 52 |
| Issue number | 38 |
| DOIs | |
| Publication status | Published - Sep 16 1996 |
Fingerprint
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 journal › Article
}
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 -