Journal
ORGANOMETALLICS
Volume 36, Issue 14, Pages 2581-2587Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.7b00152
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Funding
- Welch Foundation [AA-1846]
- NSF-REU [CHE-1359231]
- Australian Research Council [FT160100007]
- La Trobe University
- Baylor University
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1359231] Funding Source: National Science Foundation
- Australian Research Council [FT160100007] Funding Source: Australian Research Council
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The unsaturated antiaromatic BC4 heterocycle pentaphenylborole has been shown to have diverse reactivity with a variety of substrates, including the insertion of polar functional groups into the ring as a route to conjugated boracycles. This work investigates the reactivity of a selection of epoxides with pentaphenylborole, both computationally and experimentally, revealing that the substitution is highly influential on the reaction outcome. Specifically, isobutylene oxide results in protodeborylation to a borabutadiene chain attributed to the acidic beta-hydrogen atoms, 1,1-diphenylethylene oxide inserts the C2O unit to furnish a BOC6 heterocycle, and cyclohexene oxide inserts two epoxides to form an unusual BC8O2 ring. The last two species represent rare boron-containing rings of eight atoms or greater, with the 11-membered species being only the second reported and the first crystallographically characterized.
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