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Title
Japanese: 
English:Formation of an Isolable Divinylborinium Ion through Twofold 1,2-Carboboration between a Diarylborinium Ion and Diphenylacetylene 
Author
Japanese: 田中直樹, 庄子良晃, Daisuke Hashizume, Manabu Sugimoto, 福島孝典.  
English: Naoki Tanaka, Yoshiaki Shoji, Daisuke Hashizume, Manabu Sugimoto, Takanori Fukushima.  
Language English 
Journal/Book name
Japanese: 
English:Angewandte Chemie International Edition 
Volume, Number, Page Volume 56    Issue 19    Page 5312-5316
Published date May 2, 2017 
Publisher
Japanese: 
English: 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
Official URL http://onlinelibrary.wiley.com/wol1/doi/10.1002/anie.201701730/full
 
DOI https://doi.org/10.1002/anie.201701730
Abstract Borinium ions, that is, two-coordinate boron cations, are the most electron-deficient isolable boron compounds. As borinium ions have only four formal valence electrons on boron, they should show a strong tendency to accept electron pairs on the boron atom to fill its valence shell. Thus chemical reactions of borinium ions are expected to give products in which the coordination number of boron is increased from two to three or four. However, contrary to this expectation, we found that the dimesitylborinium ion (Mes2B+) undergoes twofold 1,2-carboboration reactions with two equivalents of diphenylacetylene to yield an unprecedented borinium ion (1+) with two substituted vinyl groups on the boron center. NMR spectroscopy and X-ray diffraction analysis of 1+, together with electronic-structure calculations, revealed that the positive charge is delocalized over the entire π-conjugated system. The fact that the chemical transformation of a borinium ion gives rise to a different borinium ion without a change in the coordination number is remarkable and should provide new insight into the chemistry of the Group 13 elements.

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