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'.
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U2 - 10.1016/0040-4020(96)00738-7
DO - 10.1016/0040-4020(96)00738-7
M3 - Article
AN - SCOPUS:0030590473
VL - 52
SP - 12399
EP - 12408
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 38
ER -