Nuclear magnetic resonance spectra of some 2,6-disubstituted spiro[3.3]heptane derivatives |
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| Authors: | AJ De Hoog LA Hulshof J Luotenburg |
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| Institution: | Departments of Organic Chemistry, The University, Zernikelaan, Paddepoel, Groningen, The Netherlands;The Gorlaeus Laboratories, The University, Leiden, The Netherlands |
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| Abstract: | Analysis of the full splitting pattern of the 100 MHz 1H-NMR spectra of diethyl - 2,6 -dibromospiro3.3]heptane - 2,6 - dicarboxylate (3) in chloroform and benzene and the 220 MHz 1H-NMR spectrum of dimethylspiro3.3]heptane - 2,6 - dicarboxylate (2) in naphthalene has been carried out. Puckering of the cyclobutane rings is revealed. Reasonable agreement with an X-ray study on Fecht acid (1) and with the data from the 1C-NMR spectra of compounds 2 and 3 has been obtained. The temperature dependency of the 1H-NMR spectra of 2, 3 and the symmetrically substituted tetraethylspiro3.3]heptane - 2,2,6,6 - tetracarboxylate (4) has been investigated and is discussed in terms of conformational interconversion. |
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