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Borinium, borenium, and boronium ions: synthesis, reactivity, and applications
Warren E Piers1, Sara C Bourke, Korey D Conroy
1Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, AB, T2N 1N4, Canada. wpiers@ucalgary.ca
Abstract:
Boron cations are elusive and highly electrophilic species that play a key role in the chemistry of boron. Despite early interest in the chemistry of boron cations, until recently they have largely remained chemical curiosities. However, hints at harnessing their potential as potent electrophiles have begun to appear and developments in weakly coordinating anion technology suggest that this is an area of research that is ripe for exploration. It has been nearly 20 years since the last major review on boron cations; herein we summarize the progress in the area since that time.
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Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
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