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- Title
Strain‐Release Pentafluorosulfanylation and Tetrafluoro(aryl)sulfanylation of [1.1.1]Propellane: Reactivity and Structural Insight**.
- Authors
Kraemer, Yannick; Ghiazza, Clément; Ragan, Abbey N.; Ni, Shengyang; Lutz, Sigrid; Neumann, Elizabeth K.; Fettinger, James C.; Nöthling, Nils; Goddard, Richard; Cornella, Josep; Pitts, Cody Ross
- Abstract
We leveraged the recent increase in synthetic accessibility of SF5Cl and Ar−SF4Cl compounds to combine chemistry of the SF5 and SF4Ar groups with strain‐release functionalization. By effectively adding SF5 and SF4Ar radicals across [1.1.1]propellane, we accessed structurally unique bicyclopentanes, bearing two distinct elements of bioisosterism. Upon evaluating these "hybrid isostere" motifs in the solid state, we measured exceptionally short transannular distances; in one case, the distance rivals the shortest nonbonding C⋅⋅⋅C contact reported to date. This prompted SC‐XRD and DFT analyses that support the notion that a donor‐acceptor interaction involving the "wing" C−C bonds is playing an important role in stabilization. Thus, these heretofore unknown structures expand the palette for highly coveted three‐dimensional fluorinated building blocks and provide insight to a more general effect observed in bicyclopentanes.
- Subjects
FUNCTIONAL groups; X-ray diffraction
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 48, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202211892