Diverse Reactivity of Dienes with Pentaphenylborole and 1‐Phenyl‐2,3,4,5‐Tetramethylborole Dimer

Autor:	Khadilah H. M. Al Furaiji, Caleb D. Martin, Jason L. Dutton, O. Tara Liyanage, J. J. Baker, David J. D. Wilson
Rok vydání:	2018
Předmět:	Bicyclic molecule Diene 010405 organic chemistry Dimer Organic Chemistry General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis Cycloaddition 0104 chemical sciences chemistry.chemical_compound Monomer chemistry Moiety Reactivity (chemistry) Borole
Zdroj:	Chemistry – A European Journal. 25:1581-1587
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201805151
Popis:	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.
Databáze:	OpenAIRE
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