Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SF5- and CF3SF4-containing [2]staffanes

Autor: Jón Atiba Buldt, Wang-Yeuk Kong, Yannick Kraemer, Masiel M. Belsuzarri, Ansh Hiten Patel, James C. Fettinger, Dean J. Tantillo, Cody Ross Pitts
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 20, Iss 1, Pp 3134-3143 (2024)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.20.259
Popis: Selectivity in radical chain oligomerizations involving [1.1.1]propellane – i.e., to make [n]staffanes – has been notoriously challenging to control when n > 1 is desired. Herein, we report selective syntheses of SF5- and CF3SF4-containing [2]staffanes from SF5Cl and CF3SF4Cl, demonstrating cases whereby oligomerization is preferentially truncated after incorporation of two bicyclopentane (BCP) units. Synthetic and computational studies suggest this phenomenon can be attributed to alternating radical polarity matching. In addition, single-crystal X-ray diffraction (SC-XRD) data reveal structurally interesting features of the CF3SF4-containing [2]staffane in the solid state.
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