Intramolecular bridging of calix[4]arene dialdoximes

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• 作者：Marké ; ta Zají ; cov&aacute ; ^a ; V&aacute ; clav Eigner^b ; Jan Budka^a ; Pavel Lhot&aacute ; k^a ; ^{lhotakp@vscht.cz" class="auth_mail" title="E-mail the corresponding author}
• 关键词：NVGATQUMIAQVNN-UHFFFAOYSA-N ; NVGATQUMIAQVNN-UHFFFAOYSA-N ; OOHXDMDOPJXPHS-GCQSSKKOSA-N ; VORJDRMNOZHJJB-UHFFFAOYSA-N ; XPCSUSKKDQZYFZ-UHFFFAOYSA-N ; BEYVXICEAHAQHN-UHFFFAOYSA-N ; WGUXXYZDWRNVAM-DITNJDIQSA-N ; YKNAFRAKJVXHRS-DBMXBCQFSA-N ; PHPZVVOYQPNVGG-ZAPDOKAZSA-N ; RPSDMNRAUZSEMZ-XHVGDULWSA-N ; OOHXDMDOPJXPHS-GCQSSKKOSA-N ; JJYQEKZDWWUIQB-UHFFFAOYSA-N
• 刊名：Tetrahedron Letters
• 出版年：2015
• 出版时间：7 October 2015
• 年：2015
• 卷：56
• 期：41
• 页码：5529-5532
• 全文大小：654 K

文摘

A novel method for the intramolecular bridging of calix[4]arenes, based on the reductive coupling of dialdoximes, is described. Reaction of the distal dialdoxime, immobilized in the cone conformation, using Zn/TiCl₄ afforded a calixarene with a 1,2-diaminoethane bridge and possessing meso stereochemistry. The reaction was found to be very sensitive to the conformation of the starting calixarene as evident by the absence of similar products in the 1,3-alternate conformation. meso-Diamino-bridged calixarenes represent unique synthetic intermediates with possible application in the design of new receptors.