Preparation of Tris(spiroorthocarbonate) Cyclophanes as Back to Back Ditopic Hosts
Twin-bowl-shaped tris(spiroorthocarbonate) cyclophanes were designed and prepared as ditopic hosts for electrically neutral or electron-rich guests. Preparation of the desired cyclophanes was achieved by cyclotrimerization of 2,2′,3,3′-tetrahydroxy-1,1′-binaphthyl (THB) via the transesterification o...
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Published in | Organic letters Vol. 15; no. 9; pp. 2164 - 2167 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
03.05.2013
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | Twin-bowl-shaped tris(spiroorthocarbonate) cyclophanes were designed and prepared as ditopic hosts for electrically neutral or electron-rich guests. Preparation of the desired cyclophanes was achieved by cyclotrimerization of 2,2′,3,3′-tetrahydroxy-1,1′-binaphthyl (THB) via the transesterification of tetraphenyl orthocarbonate or dichlorodiphenoxymethane. In those reactions, bis(spiroorthocarbonate) cyclophane containing two THB units was also formed as the kinetically favored product. The spiroorthocarbonate twin bowl exhibited ditopic molecular recognition toward fullerene C60 in the crystalline state. |
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Bibliography: | KAKEN ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol4006882 |