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Ring Expansion Reactions of Electron-Rich Boron-Containing Heterocycles

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Author
Piers, Warren E.
Araneda, Juan F.
Sgro, Michael J.
Parvez, Masood
Accessioned
2016-04-13T07:47:23Z
Available
2016-04-13T07:47:23Z
Issued
2015-06-16
Type
journal article
Metadata
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Abstract
The 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.
Grantingagency
NSERC
Refereed
Yes
This 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.
 
Citation
Organometallics 2015, 34, 3408−3413.
Department
Chemistry
Faculty
Science
Institution
University of Calgary
Publisher
American Chemical Society
Doi
http://dx.doi.org/10.1021/acs.organomet.5b00390
http://dx.doi.org/10.11575/PRISM/35410
Uri
http://hdl.handle.net/1880/51142
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