1. Coordination and Ring Expansion of 1,2-Dipolar Molecules with 9-Phenyl-9-borafluorene
- Author
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Venkata A. K. Adiraju, Kristen R. Bluer, Sam Yruegas, Alba Pujol, Caleb D. Martin, and Leif E. Laperriere
- Subjects
chemistry.chemical_classification ,Ketone ,Nitrile ,010405 organic chemistry ,Organic Chemistry ,Imine ,Ketene ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Aldehyde ,0104 chemical sciences ,Adduct ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,Polymer chemistry ,Moiety ,Physical and Theoretical Chemistry - Abstract
The reactivity of 9-phenyl-9-borafluorene with a series of 1,2-dipolar organic molecules is investigated, revealing that either adducts or seven-membered heterocycles are generated. A nitrile, imine, and isonitrile formed the corresponding coordination complexes that showed no evidence of conversion to ring expanded products. An aldehyde, ketone, and ketene inserted the C═O moiety into the endocyclic B–C bond resulting in BOC5 boracycles. Isocyanates inserted either C═N or C═O depending on the polarization of the substrate with the former being the only substrate to generate a BNC5 ring system. The results demonstrate the potential of 9-borafluorenes as effective reagents to generate seven-membered boracycles with a biphenyl backbone.
- Published
- 2018
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