Metal-free Trans-imination Using Iminoiodane
2019-08
Loading...
View/Download File
Persistent link to this item
Statistics
View StatisticsJournal Title
Journal ISSN
Volume Title
Title
Metal-free Trans-imination Using Iminoiodane
Authors
Published Date
2019-08
Publisher
Type
Thesis or Dissertation
Abstract
Iminoiodanes are useful nitrene precursors and effective oxidants in the reactions with various organic substrates. Most of the known reactions of iminoiodanes are carried in the presence of transition metal catalysts, required for the in-situ generation of active metal-nitrenoid species. Recently, several groups have reported the aziridination of olefines, C-H amination of alkanes, and imination of aldehydes using iminoiodanes under metal-free conditions. However, the imination of sulfides using iminoiodanes under metal-free condition is still unknown. Herein, we report the new reaction of metal free trans-imination reaction of sulfides using iminoiodanes in the presence of catalytic amounts of elemental iodine. The trans-imination reactions of various alkyl or aryl sulfides proceed at room temperature to give the corresponding sulfilimines in low to good yields. The reaction of allyl sulfides under similar conditions proceeds as [2,3]-sigmatropic rearrangement to give the corresponding allyl sulfonamides in good yields. The same condition using triphenyl phosphine instead of sulfides produced iminophosphorane in good yield, and the product was confirmed by X-ray crystallography.
Keywords
Description
University of Minnesota M.S. thesis. August 2019. Major: Chemistry. Advisor: Viktor Zhdankin. 1 computer file (PDF); vi, 71 pages.
Related to
Replaces
License
Series/Report Number
Funding information
Isbn identifier
Doi identifier
Previously Published Citation
Suggested citation
Makitalo, Cody. (2019). Metal-free Trans-imination Using Iminoiodane. Retrieved from the University Digital Conservancy, https://hdl.handle.net/11299/208942.
Content distributed via the University Digital Conservancy may be subject to additional license and use restrictions applied by the depositor. By using these files, users agree to the Terms of Use. Materials in the UDC may contain content that is disturbing and/or harmful. For more information, please see our statement on harmful content in digital repositories.