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New [4.4]Cyclophane Diketals, Monoketones, and Diketones: Design, Synthesis, and Structural Analysis
Author(s) -
Bogdan Niculina,
Grosu Ion,
Condamine Eric,
Toupet Loïc,
Ramondenc Yvan,
SilaghiDumitrescu Ioan,
Plé Gérard,
Bogdan Elena
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700343
Subject(s) - cyclophane , chemistry , reactivity (psychology) , nuclear magnetic resonance spectroscopy , intermolecular force , stereochemistry , hydrolysis , molecular model , crystallography , computational chemistry , molecule , organic chemistry , medicine , alternative medicine , pathology
The synthesis of some new [4.4]cyclophane diketals, monoketones, and diketones in good yields is reported along with the unusually low reactivity towards hydrolysis of the spiro‐1,3‐dioxane rings connected to the cyclophane bridges. The structural analysis carried out by X‐ray diffraction, NMR spectroscopy, and mass spectrometry shows significant intra‐ and intermolecular π–π and C–H–π interactions. The rotation of the aromatic rings and the flipping of the bridges have been investigated by molecular modeling and variable‐temperature NMR experiments. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)