The cyclopropylcarbinyl route to γ-silyl carbocations

Xavier Creary
Beilstein J. Org. Chem. 2019, 15, 1769–1780. https://doi.org/10.3762/bjoc.15.170

Supporting Information

Full experimental details, 1H and 13C NMR spectra of new compounds, and M062X/6-311+G** computational studies are presented as Supporting Information.

Supporting Information File 1: Experimental details and 1H and 13C NMR spectra of new compounds.
Format: PDF Size: 6.6 MB Download
Supporting Information File 2: M062X/6-611+G** calculated structures, energies, and Cartesian coordinates for carbocations and transition states.
Format: PDF Size: 1.8 MB Download

Cite the Following Article

The cyclopropylcarbinyl route to γ-silyl carbocations
Xavier Creary
Beilstein J. Org. Chem. 2019, 15, 1769–1780. https://doi.org/10.3762/bjoc.15.170

How to Cite

Creary, X. Beilstein J. Org. Chem. 2019, 15, 1769–1780. doi:10.3762/bjoc.15.170

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 215.8 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Larmore, S. P.; Champagne, P. A. Substituent Effects on the Equilibria between Cyclopropylcarbinyl, Bicyclobutonium, Homoallyl, and Cyclobutyl Cations. The Journal of organic chemistry 2024, 89, 8146–8156. doi:10.1021/acs.joc.4c00810
  • Long, P.-W.; He, T.; Klare, H. F. T.; Oestreich, M. Skeletal Rearrangements Involving Cyclopropyl- and Alkene-Stabilized Silylium Ions. Synlett 2023, 35, 941–951. doi:10.1055/a-2188-1842
  • Demchuk, O. P.; Bobovskyi, B. V.; Vashchenko, B. V.; Hryshchuk, O. V.; Skreminskyi, A.; Chernykh, A. V.; Moskvina, V. S.; Hordiyenko, O. V.; Volochnyuk, D. M.; Grygorenko, O. O. 3‐Fluoroalkyl (CF3, CHF2, CH2F) Cyclobutane‐Derived Building Blocks for Medicinal Chemistry: Synthesis and Physicochemical Properties. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202300292
  • Larmore, S. P.; Champagne, P. A. Cyclopropylcarbinyl-to-Homoallyl Carbocation Equilibria Influence the Stereospecificity in the Nucleophilic Substitution of Cyclopropylcarbinols. The Journal of organic chemistry 2023, 88, 6947–6954. doi:10.1021/acs.joc.3c00257
  • Moreira, V. M. doi:10.1002/9781119608288.ch6
  • Kelly, C. B.; Milligan, J. A.; Tilley, L. J.; Sodano, T. M. Bicyclobutanes: from curiosities to versatile reagents and covalent warheads. Chemical science 2022, 13, 11721–11737. doi:10.1039/d2sc03948f
  • Fernandes, A. J.; Panossian, A.; Michelet, B.; Martin-Mingot, A.; Leroux, F. R.; Thibaudeau, S. CF 3 -substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry. Beilstein journal of organic chemistry 2021, 17, 343–378. doi:10.3762/bjoc.17.32
  • Demchuk, O. P.; Hryshchuk, O. V.; Vashchenko, B. V.; Trofymchuk, S. A.; Melnykov, K. P.; Skreminskiy, A.; Volochnyuk, D. M.; Grygorenko, O. O. Fluoroalkyl-Containing 1,2-Disubstituted Cyclobutanes: Advanced Building Blocks for Medicinal Chemistry. European Journal of Organic Chemistry 2020, 2021, 87–95. doi:10.1002/ejoc.202001345
  • Hari, D. P.; Abell, J. C.; Fasano, V.; Aggarwal, V. K. Ring-Expansion Induced 1,2-Metalate Rearrangements: Highly Diastereoselective Synthesis of Cyclobutyl Boronic Esters. Journal of the American Chemical Society 2020, 142, 5515–5520. doi:10.1021/jacs.0c00813
  • Roy, A.; Bonetti, V.; Wang, G.; Wu, Q.; Klare, H. F. T.; Oestreich, M. Silylium-Ion-Promoted Ring-Opening Hydrosilylation and Disilylation of Unactivated Cyclopropanes. Organic letters 2020, 22, 1213–1216. doi:10.1021/acs.orglett.0c00173
Other Beilstein-Institut Open Science Activities