Investigating dimeric boroles as sources of monomers.

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Boroles are 4π electron, antiaromatic, BC₄ systems that boast an array of interesting reactivity, including ring expansion, ring opening, Diels-Alder, and redox chemistry. The majority of publications in the last 10 years has been focused on the reactivity of monomeric boroles while dimeric boroles, which lack the bulky aryl substituents on the butadiene backbone, have been left largely unexplored. 1-Phenyl-2,3,4,5-tetramethylborole was synthesized in 1988 and is a borole dimer which can theoretically be utilized as a less bulky borole unit upon “cracking,” much like a cyclopentadiene dimer. Only four papers have been published on the reactivity 1-phenyl-2,3,4,5-tetramethylborole in the last 40 years. This thesis details the investigation into 1-phenyl-2,3,4,5-tetramethylborole dimer and its ability to act as a monomer upon “cracking” at higher temperatures.

Borole. Dimers. Diels-Alder. Ring Expansion. 1,2-Thiaborine.