Journal of the American Chemical Society
Journal of the American Chemical Society
4 years ago

Isolation of an Antiaromatic Singlet Cyclopentadienyl Zwitterion

Isolation of an Antiaromatic Singlet Cyclopentadienyl Zwitterion
Iris Trosien, Wolfram Sander, Joel Mieres-Perez, Paolo Costa
The reaction of triplet tetrachlorocyclopentadienylidene with BF3 in rare gas matrices yields a zwitterion consisting of a cyclopentadienyl cation bearing a positive charge and a negatively charged BF3 unit. IR and UV–vis spectra as well as the absence of EPR signals demonstrate a singlet ground state of the zwitterion, and its calculated geometry and magnetic properties clearly reveal a strong antiaromatic character. The zwitterion is highly labile and by visible or IR irradiation rearranges via a 1,2-fluorine migration from boron to carbon. Interaction with a second molecule of BF3 stabilizes the zwitterion and suppresses the fluorine migration, thus providing a convenient and efficient synthesis of an antiaromatic molecule under very mild conditions.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05807

DOI: 10.1021/jacs.7b05807

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