Journal
CHEM
Volume 4, Issue 4, Pages 795-806Publisher
CELL PRESS
DOI: 10.1016/j.chempr.2018.01.011
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology and Japan Society for the Promotion of Science KAKENHI [JP16H06591, JP15H03790, JP16K13968, JP16H01125, JP15K17818]
- Cooperative Research Program of Network Joint Research Center for Materials and Devices.''
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On the basis of the intramolecular core-shell strategy,'' we designed dihydropyracylene with two spiro(dibenzocycloheptatriene) units, for which theoretical calculations predicted a very weak C-C bond with a bond length around 1.8 angstrom. This bond is expanded by the forced adoption of an eclipsed conformation and by angle strain through a scissor effect.'' The highly strained hydrocarbon was isolated as a thermally stable compound with no signs of diradical contribution because the weak C-C bond (core) is protected by the shape-persistent fusedring structure (shell). A Raman shift corresponding to the C-C stretching vibration (587 cm(-1)) was very different from that for ethane (993 cm(-1)). The bond length determined by X-ray (1.806(2) angstrom) was greater than the shortest nonbonded intramolecular CC contact (1.80(2) angstrom). The assumed limit for a C-C bond (1.803 angstrom) by supposing linear correlation between bond length and bond-dissociation energy for covalent bonding was proven to be invalid.
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