Ring Expansion Reactions of Electron-Rich Boron-Containing Heterocycles

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dc.contributor.authorPiers, Warren E.
dc.contributor.authorAraneda, Juan F.
dc.contributor.authorSgro, Michael J.
dc.contributor.authorParvez, Masood
dc.date.accessioned2016-04-13T07:47:23Z
dc.date.available2016-04-13T07:47:23Z
dc.date.issued2015-06-16
dc.descriptionThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Organometallics, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acs.organomet.5b00390.en_US
dc.description.abstractThe potassium salts of the dianions of isomeric compounds bis-benzocycloborabutylidene, 1, and the ladder diborole 2 were reacted with carbon dioxide (CO2) and carbon monoxide (CO) and the ring expansion products fully characterized. Both dianions 1 and 2 react rapidly with carbon dioxide to form the same insertion product, 3, in which the boron-containing rings are expanded to six-membered rings. Compound 3 is a B–O analogue of binaphtholate. Only dianion 2 reacts cleanly with the weaker electrophile CO, producing a product (4) 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 3 and 4 are reported, and reasonable paths to their formation are proposed.en_US
dc.description.grantingagencyNSERCen_US
dc.description.refereedYesen_US
dc.identifier.citationOrganometallics 2015, 34, 3408−3413.en_US
dc.identifier.doi10.1021/acs.organomet.5b00390
dc.identifier.doihttp://dx.doi.org/10.11575/PRISM/35410
dc.identifier.urihttp://hdl.handle.net/1880/51142
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.publisher.departmentChemistryen_US
dc.publisher.facultyScienceen_US
dc.publisher.institutionUniversity of Calgaryen_US
dc.titleRing Expansion Reactions of Electron-Rich Boron-Containing Heterocyclesen_US
dc.typejournal article
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