Dokument-ID Dokumenttyp Verfasser/Autoren Herausgeber Haupttitel Abstract Auflage Verlagsort Verlag Erscheinungsjahr Seitenzahl Schriftenreihe Titel Schriftenreihe Bandzahl ISBN Quelle der Hochschulschrift Konferenzname Quelle:Titel Quelle:Jahrgang Quelle:Heftnummer Quelle:Erste Seite Quelle:Letzte Seite URN DOI Abteilungen OPUS4-14250 unpublished Arrowsmith, Merle; Böhnke, Julian; Braunschweig, Holger; Celik, Mehmet; Claes, Christina; Ewing, William; Krummenacher, Ivo; Lubitz, Katharina; Schneider, Christoph Neutral Diboron Analogues of Archetypal Aromatic Species by Spontaneous Cycloaddition Among the numerous routes organic chemists have developed to synthesize benzene derivatives and heteroaro- matic compounds, transition-metal-catalyzed cycloaddition reactions are the most elegant. In contrast, cycloaddition reactions of heavier alkene and alkyne analogues, though limited in scope, proceed uncatalyzed. In this work we present the first spontaneous cycloaddition reactions of lighter alkene and alkyne analogues. Selective addition of unactivated alkynes to boron-boron multiple bonds under ambient con- ditions yielded diborocarbon equivalents of simple aromatic hydrocarbons, including the first neutral 6p-aromatic dibora- benzene compound, a 2 p-aromatic triplet biradical 1,3-dibor- ete, and a phosphine-stabilized 2 p-homoaromatic 1,3-dihydro- 1,3-diborete. DFT calculations suggest that all three com- pounds are aromatic and show frontier molecular orbitals matching those of the related aromatic hydrocarbons, C6H6 and C4H42+, and homoaromatic C4H5+. 2016 4 urn:nbn:de:bvb:20-opus-142500 10.1002/anie.201602384 Institut für Anorganische Chemie OPUS4-13822 Wissenschaftlicher Artikel Arrowsmith, Merle; Böhnke, Julian; Braunschweig, Holger; Celik, Mehmet; Claes, Christina; Ewing, William; Krummenacher, Ivo; Lubitz, Katharina; Schneider, Christoph Neutral Diboron Analogues of Archetypal Aromatic Species by Spontaneous Cycloaddition Among the numerous routes organic chemists have developed to synthesize benzene derivatives and heteroaro- matic compounds, transition-metal-catalyzed cycloaddition reactions are the most elegant. In contrast, cycloaddition reactions of heavier alkene and alkyne analogues, though limited in scope, proceed uncatalyzed. In this work we present the first spontaneous cycloaddition reactions of lighter alkene and alkyne analogues. Selective addition of unactivated alkynes to boron-boron multiple bonds under ambient con- ditions yielded diborocarbon equivalents of simple aromatic hydrocarbons, including the first neutral 6 π-aromatic dibora- benzene compound, a 2  π-aromatic triplet biradical 1,3-dibor- ete, and a phosphine-stabilized 2  π-homoaromatic 1,3-dihydro- 1,3-diborete. DFT calculations suggest that all three com- pounds are aromatic and show frontier molecular orbitals matching those of the related aromatic hydrocarbons, C\(_6\)H\(_6\) and C\(_4\)H\(_4\)\(^{2+}\), and homoaromatic C\(_4\)H\(_5\)\(^+\). 2016 11271-11275 Angewandte Chemie, International Edition 55 urn:nbn:de:bvb:20-opus-138226 10.1002/anie.201602384 Institut für Anorganische Chemie