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Title: Ring Expansion Reactions of Electron-Rich Boron-Containing Heterocycles
Authors: Piers, Warren E.
Araneda, Juan F.
Sgro, Michael J.
Parvez, Masood
Issue Date: 16-Jun-2015
Publisher: American Chemical Society
Citation: Organometallics 2015, 34, 3408−3413.
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.
Description: 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
Appears in Collections:Piers, Warren E.

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