Synthesis of Unique Cagelike Thiacalix[4]arene Derivatives in a 1,3-Alternate Conformation

A novel type of doubly bridged thiacalix[4]arenes in the 1,3-alternate conformation has been prepared by direct aminolysis reaction of easily accessible thiacalix[4]arene tetraacetates with α,ω-diamines. Despite the high excess of diamine, both sites of a 1,3-alternate conformer can be intramolecula...

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Veröffentlicht in:	Journal of organic chemistry 2006-07, Vol.71 (14), p.5404-5406
Hauptverfasser:	Št'astný, Václav, Stibor, Ivan, Císařová, Ivana, Sýkora, Jan, Pojarová, Michaela, Lhoták, Pavel
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Organic chemistry
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container_title	Journal of organic chemistry
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creator	Št'astný, Václav Stibor, Ivan Císařová, Ivana Sýkora, Jan Pojarová, Michaela Lhoták, Pavel
description	A novel type of doubly bridged thiacalix[4]arenes in the 1,3-alternate conformation has been prepared by direct aminolysis reaction of easily accessible thiacalix[4]arene tetraacetates with α,ω-diamines. Despite the high excess of diamine, both sites of a 1,3-alternate conformer can be intramolecularly bridged to form the cagelike structures in high yields. Optimum results were obtained using 1,2-ethanediamine as bridging units. X-ray analysis of the novel cagelike molecules revealed a highly preorganized array of −C(O)−NH− bonds pointing to the interior of the cavity.
doi_str_mv	10.1021/jo0607358
format	Article
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Org. Chem</addtitle><date>2006-07-07</date><risdate>2006</risdate><volume>71</volume><issue>14</issue><spage>5404</spage><epage>5406</epage><pages>5404-5406</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A novel type of doubly bridged thiacalix[4]arenes in the 1,3-alternate conformation has been prepared by direct aminolysis reaction of easily accessible thiacalix[4]arene tetraacetates with α,ω-diamines. Despite the high excess of diamine, both sites of a 1,3-alternate conformer can be intramolecularly bridged to form the cagelike structures in high yields. Optimum results were obtained using 1,2-ethanediamine as bridging units. X-ray analysis of the novel cagelike molecules revealed a highly preorganized array of −C(O)−NH− bonds pointing to the interior of the cavity.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16808538</pmid><doi>10.1021/jo0607358</doi><tpages>3</tpages></addata></record>
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title	Synthesis of Unique Cagelike Thiacalix[4]arene Derivatives in a 1,3-Alternate Conformation
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