Browsing Thompson, Alison by Author "5a8fb5e7-c762-47c2-96eb-d70078f6315b"

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  • Activation and Deprotection of F-BODIPYs using Boron Trihalides 

    Lundrigan, Travis, Cameron, T. Stanley, Thompson, Alison. (2014). Activation and deprotection of F-BODIPYs using boron trihalides. Chemical Communications, 50(53), 7028-7031. DOI: 10.1039/C4CC02706J
    The activation of F-BODIPYs with boron trihalides, followed by treatment with a nuclephile, effects facile substitution at boron; using water as the nucleophile promotes deprotective removal of the–BF2 moiety and thereby ...

  • Deuteration and Tautomeric Reactivity of the 1-Methyl Functionality of Free-base Dipyrrins 

    Groves, B. R., Cameron, T. S., & Thompson, A. (2017). Deuteration and tautomeric reactivity of the 1-methyl functionality of free-base dipyrrins. Organic & biomolecular chemistry, 15(37), 7925-7935. DOI: 10.1039/C7OB01278K
    Regioselective reactivity of the 1-methyl group of free-base dipyrrins is explored, including discussion of tautomerism to provide exocyclic alkenyl reactivity. Deuterium is installed such as to generate dipyrrins substituted ...

  • An Improved Method for the Synthesis of F-BODIPYs from Dipyrrins and Bis(dipyrrin)s 

    Lundrigan, T., Baker, A. E., Longobardi, L. E., Wood, T. E., Smithen, D. A., Crawford, S. M., ... & Thompson, A. (2012). An Improved Method for the Synthesis of F-BODIPYs from Dipyrrins and Bis (dipyrrin) s. Organic letters, 14(8), 2158-2161. DOI: 10.1021/ol300681w
    An improved methodology for the synthesis of F-BODIPYs from dipyrrins and bis(dipyrrin)s is reported. This strategy employs lithium salts of dipyrrins as intermediates that are then treated with only one equivalent of boron ...

  • Microwave-assisted reduction of F-BODIPYs and dipyrrins to generate dipyrromethanes 

    Melanson, J. A., Smithen, D. A., Cameron, T. S., & Thompson, A. (2013). Microwave-assisted reduction of F-BODIPYs and dipyrrins to generate dipyrromethanes. Canadian Journal of Chemistry, 92(8), 688-694. doi: https://doi.org/10.1139/cjc-2013-0341
    The reduction of BODIPYs and dipyrrins to dipyrromethanes, via a reaction involving ethylene glycol and sodium methoxide, is reported. When benzyl alcohol is used in place of ethylene glycol, the addition of 2,4-dinitrop ...

  • Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF2 removal. 

    Smithen, D. A., Baker, A. E., Offman, M., Crawford, S. M., Cameron, T. S., & Thompson, A. (2012). Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF2 removal. The Journal of organic chemistry, 77(7), 3439-3453. DOI: 10.1021/jo3002003
    We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of ...