Bridgehead dienes. Thermal generation of the bicyclo[3.3.1]nona-1(2),4(5)-diene (ZZ) ring system |
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| Affiliation: | 1. Department of Chemical Engineering, Tsinghua University, Beijing 100084, China;2. MOE Key Lab of Industrial Biocatalysis, Tsinghua University, Beijing 100084, China |
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| Abstract: | The bicyclo[3.3.1]nona-1(1),4(5)-diene (ZZ) ring system has been generated by intramolecular Diels-Alder cycloaddition of methyl 7-methylene-non-2-yn-8-enoate. This highly strained bridgehead diene undergoes a homo 1,5-hydrogen shift to yield a [3.3.1] propellane product. |
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