Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 6, Pages 1581-1587Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201805151
Keywords
anti-aromaticity; boroles; boron heterocycles; cycloaddition; Diels-Alder reactions
Categories
Funding
- Welch Foundation [AA-1846]
- National Science Foundation (CAREER) [1753025]
- Australian Research Council [FT16010007]
- NCI
- Intersect
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1753025] Funding Source: National Science Foundation
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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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