Journal
NATURE CHEMISTRY
Volume 8, Issue 3, Pages 220-224Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.2438
Keywords
-
Categories
Funding
- European Research Council Advanced Grant CEMAS [291194]
- European Union project PAMS [610446]
- Initial Training Network QTea program [317485]
- Initial Training Network ACRITAS program [317348]
- Spanish Ministry of Science and Competitiveness [MAT2013-46593-C6-6-P]
Ask authors/readers for more resources
The Bergman cyclization is one of the most fascinating rearrangements in chemistry, with important implications in organic synthesis and pharmacology. Here we demonstrate a reversible Bergman cyclization for the first time. We induced the on-surface transformation of an individual aromatic diradical into a highly strained ten-membered diyne using atomic manipulation and verified the products by non-contact atomic force microscopy with atomic resolution. The diyne and diradical were stabilized by using an ultrathin NaCl film as the substrate, and the diyne could be transformed back into the diradical. Importantly, the diradical and the diyne exhibit different reactivity, electronic, magnetic and optical properties associated with the changes in the bond topology, and spin multiplicity. With this reversible, triggered Bergman cyclization we demonstrated switching on demand between the two reactive intermediates by means of selective C-C bond formation or cleavage, which opens up the field of radical chemistry for on-surface reactions by atomic manipulation.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available