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Ring Expansion Reactions of Electron-Rich Boron-Containing Heterocycles

By Juan F. Araneda (1569991), Warren E. Piers (1569994), Michael J. Sgro (1570000) and Masood Parvez (1569997)


The potassium salts of the dianions of isomeric compounds bis-benzocycloborabutylidene, <b>1</b>, and the ladder diborole <b>2</b> were reacted with carbon dioxide (CO<sub>2</sub>) and carbon monoxide (CO) and the ring expansion products fully characterized. Both dianions <b>1</b> and <b>2</b> react rapidly with carbon dioxide to form the same insertion product, <b>3</b>, in which the boron-containing rings are expanded to six-membered rings. Compound <b>3</b> is a B–O analogue of binaphtholate. Only dianion <b>2</b> reacts cleanly with the weaker electrophile CO, producing a product (<b>4</b>) in which only one of the boron-containing rings is expanded through formal insertion of CO into a B–C bond. The X-ray structures of both <b>3</b> and <b>4</b> are reported, and reasonable paths to their formation are proposed

Topics: Biophysics, Biochemistry, Genetics, Pharmacology, Biotechnology, Evolutionary Biology, Marine Biology, Inorganic Chemistry, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, ring expansion products, dianion, insertion, ring Expansion Reactions, carbon dioxide, ladder diborole 2, CO
Year: 2015
DOI identifier: 10.1021/acs.organomet.5b00390.s001
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Provided by: FigShare
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