Doubly Bridged Calix[8]crowns

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Title:Doubly Bridged Calix[8]crowns
Creators:
Geraci, Corrada
Consoli, Grazia M. L.
Piattelli, Mario
Neri, Placido
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 6, pp. 1345-1361
Uncontrolled Keywords:Calixarenes, Conformation analysis, Host-guest chemistry, Intramolecular bridging, Calix[8]arenes, Inherent chirality, Crown ethers, Complexation

Abstract

Biscrowned calix[8]arenes were obtained by alkylation of <i>p-tert</i>-butylcalix[8]arene or calix[8]monocrowns with triethylene glycol ditosylate, in the presence of various bases. Of the 22 possible isomers, 1,4:2,5-, 1,3:2,5-, 1,4:2,3-, 1,4:5,8-, and 1,2:3,4-calix[8]biscrown-4 (<strong>3</strong>-<strong>7</strong>) were isolated in 7-30% yields. The presence of two crown bridges in 1,3:2,5- and 1,4:2,5-biscrown-4 (<strong>4</strong>, <strong>5</strong>) leads to a significant rigidness of the calix[8]arene macrocycle and implies inherent chirality. The increased preorganization of calix[8]biscrowns, with respect to monocrowns, leads to significant complexing abilities for alkali cations with a marked preference for Cs<sup>+</sup> over Na<sup>+</sup>. <p>

Title:Doubly Bridged Calix[8]crowns
Creators:
Geraci, Corrada
Consoli, Grazia M. L.
Piattelli, Mario
Neri, Placido
Uncontrolled Keywords:Calixarenes, Conformation analysis, Host-guest chemistry, Intramolecular bridging, Calix[8]arenes, Inherent chirality, Crown ethers, Complexation
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:6
Page Range:pp. 1345-1361
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041345UNSPECIFIED
ID Code:2278
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Geraci, Corrada; Consoli, Grazia M. L.; Piattelli, Mario; Neri, Placido (2004) Doubly Bridged Calix[8]crowns. Collection of Czechoslovak Chemical Communications, 69 (6). pp. 1345-1361. ISSN 0010-0765

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