Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SF<sub>5</sub>- and CF<sub>3</sub>SF<sub>4</sub>-containing [2]staffanes
Selectivity in radical chain oligomerizations involving [1.1.1]propellane - i.e., to make [<i>n</i>]staffanes - has been notoriously challenging to control when <i>n</i> > 1 is desired. Herein, we report selective syntheses of SF<sub>5</sub>- and CF<sub>3</sub>SF<sub>4</sub>-containing [2]staffanes from SF<sub>5</sub>Cl and CF<sub>3</sub>SF<sub>4</sub>Cl, 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 CF<sub>3</sub>SF<sub>4</sub>-containing [2]staffane in the solid state.
Authors
- Ansh Hiten Patel (ORCID: https://orcid.org/0009-0006-2278-9227)
- Yannick Kraemer (ORCID: https://orcid.org/0000-0002-2136-7253)
- Cody Ross Pitts (ORCID: https://orcid.org/0000-0003-1047-8924)
- Wang‐Yeuk Kong (ORCID: https://orcid.org/0000-0002-4592-0666)
- James C. Fettinger (ORCID: https://orcid.org/0000-0002-6428-4909)
- Dean Joseph Tantillo (ORCID: https://orcid.org/0000-0002-2992-8844)
- Masiel M. Belsuzarri
- Jón Atiba Buldt (ORCID: https://orcid.org/0009-0005-4900-0479)
Institutions
- University of California, Davis (US)
Publication Details
- Journal
- Beilstein Journal of Organic Chemistry
- Published
- 2024-11-29
- DOI
- https://doi.org/10.3762/bjoc.20.259
- Citations
- 7
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 1.75
Funders
- National Science Foundation
- Croucher Foundation
- Eidgenössische Technische Hochschule Zürich
- National Institutes of Health
- University of California, Davis
- National Institute of General Medical Sciences
- Division of Chemistry