We could access for the first time a 5-phosphasemibullvalene derivative via quantitative and selective photochemical di-π-methane rearrangement from the corresponding phosphabarrelene. Due to the striking analogy between phosphorus and carbon, this hitherto unknown transformation of vinyl-phosphorus species provides the possibility to prepare novel, chiral and conformationally rigid organophosphorus cage compounds in a straightforward manner.
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Pyridyl-Functionalized 1-Phosphabarrelene: Synthesis, Coordination Chemistry and Photochemical di-π-Methane Rearrangement.
Chemistry
November 2019
Institut für Chemie und Biochemie, Freie Universität Berlin, Fabeckstrasse 34/36, 14195, Berlin, Germany.
The [4+2] cycloaddition of 2-(2'-pyridyl)-4,6-diphenyl-λ -phosphinine with the highly reactive dienophile hexafluoro-2-butyne has been studied and the first pyridyl-functionalized 1-phosphabarrelene was obtained and structurally characterized. Although monodentate CF -1-phosphabarrelenes show only a poor coordination ability, the chelating nature of the novel P,N-hybrid ligand gives access to various transition-metal complexes. Upon irradiation with UV light, the pyridyl-functionalized 1-phosphabarrelene undergoes a rather selective di-π-methane rearrangement in the coordination sphere of the metal center, leading to the formation of a complex based on a hitherto unknown pyridyl-functionalized 5-phosphasemibullvalene derivative.
View Article and Find Full Text PDFExpanding the phosphorus-carbon analogy: formation of an unprecedented 5-phosphasemibullvalene derivative.
Chem Commun (Camb)
June 2016
Institut für Chemie und Biochemie - Freie Universität Berlin, Fabeckstr. 34/36, 14195 Berlin, Germany.
We could access for the first time a 5-phosphasemibullvalene derivative via quantitative and selective photochemical di-π-methane rearrangement from the corresponding phosphabarrelene. Due to the striking analogy between phosphorus and carbon, this hitherto unknown transformation of vinyl-phosphorus species provides the possibility to prepare novel, chiral and conformationally rigid organophosphorus cage compounds in a straightforward manner.
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