Strain-Release Pentafluorosulfanylation and Tetrafluoro(aryl)sulfanylation of [1.1.1]Propellane: Reactivity and Structural Insight.

ABSTRACT: We leveraged the recent increase in synthetic accessibility of SF₅ Cl and Ar-SF₄ Cl compounds to combine chemistry of the SF₅ and SF₄ Ar groups with strain-release functionalization. By effectively adding SF₅ and SF₄ Ar 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 stabilizati

SUBMITTER: Kraemer Y 

PROVIDER: S-EPMC9828730 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature