期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 28, 页码 8692-8698出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103628
关键词
biradicals; didehydronaphthalene; FT-ICR; ion-molecule reactions; reactive intermediates
资金
- National Science Foundation [103762]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0910466] Funding Source: National Science Foundation
The chemical properties of a 1,8-didehydronaphthalene derivative, the 4,5-didehydroisoquinolinium cation, were examined in the gas phase in a dual-cell Fourier-transform ion cyclotron resonance (FT-ICR) mass spectrometer. This is an interesting biradical because it has two radical sites in close proximity, yet their coupling is very weak. In fact, the biradical is calculated to have approximately degenerate singlet and triplet states. This biradical was found to exclusively undergo radical reactions, as opposed to other related biradicals with nearby radical sites. The first bond formation occurs at the radical site in the 4-position, followed by that in the 5-position. The proximity of the radical sites leads to reactions that have not been observed for related mono- or biradicals. Interestingly, some ortho-benzynes have been found to yield similar products. Since ortho-benzynes do not react via radical mechanisms, these products must be especially favorable thermodynamically.
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