En route to tetra-t-butylethylene |
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| Affiliation: | 1. High Magnetic Field Laboratory, Chinese Academy of Sciences, Hefei 230031, China;2. School of Life Sciences, University of Science and Technology of China, Hefei 230027, China;3. Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, Suzhou 215123, China;1. Chemistry Department, Lomonosov Moscow State University, Leninskie Gory, 1, 119991, Moscow (Russia);2. Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076, Tübingen (Germany);3. Albert-Ludwigs-Universitat Freiburg, Institute for Physikalische Chemie,Albertstrasse, 21, Freiburg Allemagne, 79104, (Germany);4. present address: Analytische Chemie – Elektroanalytik & Sensorik, Ruhr-Universität-Bochum, Universitäts str. 150, 44,780 Bochum (Germany) |
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| Abstract: | Triene 22 was synthesized and converted by two different routes to the tetraaldehyde 27, the first “non-bridged” derivative of 1. An X-ray analysis of 27 reveals that the CC bond is twisted by 28.6°. Attempts to prepare 1 from 27 failed, thus far. Addition of t-butyllithium to 13, subsequent reaction with ethylene oxide and further reactions led to the highly strained tri-t-butylethylethylene 33; according to force field calculations 33 has the largest fragmentation strain of all synthesized hydrocarbons of this type. |
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