AI Article Synopsis
- - The study examines how a single borole and a pair of boroles (dimer) react with 2,3-dimethyl-1,3-butadiene and 1,3-cyclohexadiene, revealing temperature-dependent behaviors in their reactivity.
- - The monomeric borole reacts at room temperature, while the dimer requires heating to break apart and engage in reactions.
- - Various products emerge from the reaction with 2,3-dimethyl-1,3-butadiene through cycloaddition processes, and 1,3-cyclohexadiene participates in a [4+2] cycloaddition; theoretical models support that boroles can act as both d
Article Abstract
The reactions of a monomeric borole and a dimeric borole with 2,3-dimethyl-1,3-butadiene and 1,3-cyclohexadiene were investigated. The monomeric borole reacted at ambient temperature whereas heat was required to crack the dimer to form the monomer and induce reactivity. 2,3-Dimethyl-1,3-butadiene reacts to give diverse products resulting from a cycloaddition process with the B-C moiety of the boroles acting as a dienophile, followed by rearrangements to furnish bicyclic species. For 1,3-cyclohexadiene, a [4+2] process is observed in which 1,3-cyclohexadiene serves as the dienophile and the boroles as the diene partner. The experimental results are corroborated with mechanistic theoretical calculations that indicate boroles can serve as either a diene or dienophile in cycloaddition reactions with dienes.
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| http://dx.doi.org/10.1002/chem.201805151 | DOI Listing |
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