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Synfacts 2010(8): 0886-0886
DOI: 10.1055/s-0030-1257836
DOI: 10.1055/s-0030-1257836
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
Stable Borepin Rings
Contributor(s):Timothy M. Swager, D. Barney WalkerA. Caruso Jr., M. A. Siegler, J. D. Tovar*
Johns Hopkins University, Baltimore, USA
Synthesis of Functionalizable Boron Containing π-Electron Materials that Incorporate Formally Aromatic Fused Borepin Rings
Angew. Chem. Int. Ed. 2010, 49: 4213-4217
Johns Hopkins University, Baltimore, USA
Synthesis of Functionalizable Boron Containing π-Electron Materials that Incorporate Formally Aromatic Fused Borepin Rings
Angew. Chem. Int. Ed. 2010, 49: 4213-4217
Further Information
Publication History
Publication Date:
22 July 2010 (online)
Key words
annulation - π-electron materials - boron
Significance
A versatile synthesis of polycyclic six π-electron borepin rings is described. In the key step the normally unstable borepin ring is ‘trapped’ using a bulky 2,4,6-triisopropylphenyl group (e.g., in the formation of 1) allowing for further synthetic elaboration under ambient conditions. The authors report several examples of these novel heterocycles in addition to the fused diborepin 2 shown above.
Comment
The reported family of stable and planar borepins may prove to be a useful precursor in the construction of new electronic materials.