1,4,5,8-Tetraacyl-1,4,5,8-tetraazadecalins: Configurational and conformational analysis in the crystal and in solution: Structure and conformation of heterocycles-12 |
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Authors: | Frans Borremans Marc Anteunis Uri Shmueli Leah Schleifer Hanna Shvo Benzion Fuchs |
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Institution: | Department of Organic Chemistry, State University of Gent, Gent, Belgium;Department of Chemistry, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel |
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Abstract: | A series of 1,4,5,8-tetraacyl-1,4,5,8-tetraazadecalins was studied and found to exist in trans form in analogy with the parent system2. Only tetraacetyltetraazadecalin (TATAD) could be obtained in both trans and cis forms, which were investigated in detail by X-ray diffraction analysis and NMR techniques, trans -TATAD (8) occurs in the crystal in a centrosymmetric double twist-boat conformation whereas cis -TATAD (9) has one ring as a flattened chair and the other as a twist boat with all the amide CO's syn-oriented. Three out of seven possible rotameric forms of 9 occur at low temperature in solution. The free energy of activation of amide rotation in trans-TATAD (8) is 14.5 kcal/mol, in contrast to ca 12kcal/mol in the unique cis isomer (9). |
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