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Synthesis and NMR Conformational Studies ofp-tert-Butyldihomooxacalix[4]arene Derivatives Bearing Pyridyl Pendant Groups at the Lower Rim

2002; Wiley; Volume: 2002; Issue: 17 Linguagem: Inglês

10.1002/1099-0690(200209)2002

1434-193X

Paula M. Marcos, José R. Ascenso, J. L. C. Pereira,

Molecular Sensors and Ion Detection

European Journal of Organic ChemistryVolume 2002, Issue 17 p. 3034-3041 Full Paper Synthesis and NMR Conformational Studies of p-tert-Butyldihomooxacalix[4]arene Derivatives Bearing Pyridyl Pendant Groups at the Lower Rim Paula M. Marcos, Paula M. Marcos pmmarcos@fc.ul.pt Faculdade de Ciências da Universidade de Lisboa, Departamento de Química/CCMM, Edifício C8, 1749-016 Lisboa, Portugal Fac. de Farmácia da Universidade de Lisboa Av. Forças Armadas, 1049-001 Lisboa, PortugalSearch for more papers by this authorJosé R. Ascenso, José R. Ascenso Instituto Superior Técnico, Complexo I, Av. Rovisco Pais, 1049-001 Lisboa, PortugalSearch for more papers by this authorJ. L. C. Pereira, J. L. C. Pereira Faculdade de Ciências da Universidade de Lisboa, Departamento de Química/CCMM, Edifício C8, 1749-016 Lisboa, PortugalSearch for more papers by this author Paula M. Marcos, Paula M. Marcos pmmarcos@fc.ul.pt Faculdade de Ciências da Universidade de Lisboa, Departamento de Química/CCMM, Edifício C8, 1749-016 Lisboa, Portugal Fac. de Farmácia da Universidade de Lisboa Av. Forças Armadas, 1049-001 Lisboa, PortugalSearch for more papers by this authorJosé R. Ascenso, José R. Ascenso Instituto Superior Técnico, Complexo I, Av. Rovisco Pais, 1049-001 Lisboa, PortugalSearch for more papers by this authorJ. L. C. Pereira, J. L. C. Pereira Faculdade de Ciências da Universidade de Lisboa, Departamento de Química/CCMM, Edifício C8, 1749-016 Lisboa, PortugalSearch for more papers by this author First published: 12 August 2002 https://doi.org/10.1002/1099-0690(200209)2002:17 3.0.CO;2-ICitations: 14Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Abstract Direct O-alkylation of p-tert-butyldihomooxacalix[4]arene (1) with 2-(chloromethyl)pyridine hydrochloride and NaH in DMF provided six of the nine possible (2-pyridylmethoxy)dihomooxacalix[4]arene conformers in the cone conformation. Mono- and tetrasubstituted derivatives were obtained, as well as all four (1,2-, 1,3-, 1,4- and 2,3-) types of disubstituted compounds. The conformations and the substitution patterns were established by NMR spectroscopy (1H, 13C, COSY, NOESY and TOCSY 1D). From the same reaction, another tetrasubstituted derivative (6) in a 1,2-alternate A conformation was also isolated and characterised. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002) Citing Literature Volume2002, Issue17September 2002Pages 3034-3041 RelatedInformation