Trityl Radicals with a Combination of the Orthogonal Functional Groups Ethyne and Carboxyl: Synthesis without a Statistical Step and EPR Characterization

Hintz H, Vanas A, Klose D, Jeschke G, Godt A (2019)
JOURNAL OF ORGANIC CHEMISTRY 84(6): 3304-3320.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Finland trityl radical (FTR) shows very attractive EPR spectroscopic properties for a manifold of applications. For most of its applications only one chemically reactive functional group is needed. The presence of three equally reactive carboxyl groups leads to FTR modifications through reactions which give statistical mixtures of 1-fold-, 2-fold-, and 3-fold-modified and unmodified FTR To avoid the side effects of such a statistical reaction-limited yields and separation challenges-we took a route to FTR-type trityl radicals with scaffold assembly by addition of an aryllithium with one type of substituent to a diarylketone with another type of substituent. This gave the two FTR-type trityl radicals 1 and 2 which carry a combination of the chemically orthogonal groups, carboxyl and triisopropylsilylethynyl. Standard column chromatography was sufficient for product isolation on all stages, whereby polar tagging helped. The EPR spectroscopic properties of the trityl radicals 1 and 2 in ethanol were determined in X and W bands. Their g anisotropy and T-1 and T-2 relaxation times make them spin labels as good as the benchmark FTR. This paper discloses also details on the synthesis of building blocks used for FTR preparation and improved access to the bare FTR scaffold.
Erscheinungsjahr
Zeitschriftentitel
JOURNAL OF ORGANIC CHEMISTRY
Band
84
Ausgabe
6
Seite(n)
3304-3320
ISSN
PUB-ID

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Hintz H, Vanas A, Klose D, Jeschke G, Godt A. Trityl Radicals with a Combination of the Orthogonal Functional Groups Ethyne and Carboxyl: Synthesis without a Statistical Step and EPR Characterization. JOURNAL OF ORGANIC CHEMISTRY. 2019;84(6):3304-3320.
Hintz, H., Vanas, A., Klose, D., Jeschke, G., & Godt, A. (2019). Trityl Radicals with a Combination of the Orthogonal Functional Groups Ethyne and Carboxyl: Synthesis without a Statistical Step and EPR Characterization. JOURNAL OF ORGANIC CHEMISTRY, 84(6), 3304-3320. doi:10.1021/acs.joc.8b03234
Hintz, H., Vanas, A., Klose, D., Jeschke, G., and Godt, A. (2019). Trityl Radicals with a Combination of the Orthogonal Functional Groups Ethyne and Carboxyl: Synthesis without a Statistical Step and EPR Characterization. JOURNAL OF ORGANIC CHEMISTRY 84, 3304-3320.
Hintz, H., et al., 2019. Trityl Radicals with a Combination of the Orthogonal Functional Groups Ethyne and Carboxyl: Synthesis without a Statistical Step and EPR Characterization. JOURNAL OF ORGANIC CHEMISTRY, 84(6), p 3304-3320.
H. Hintz, et al., “Trityl Radicals with a Combination of the Orthogonal Functional Groups Ethyne and Carboxyl: Synthesis without a Statistical Step and EPR Characterization”, JOURNAL OF ORGANIC CHEMISTRY, vol. 84, 2019, pp. 3304-3320.
Hintz, H., Vanas, A., Klose, D., Jeschke, G., Godt, A.: Trityl Radicals with a Combination of the Orthogonal Functional Groups Ethyne and Carboxyl: Synthesis without a Statistical Step and EPR Characterization. JOURNAL OF ORGANIC CHEMISTRY. 84, 3304-3320 (2019).
Hintz, Henrik, Vanas, Agathe, Klose, Daniel, Jeschke, Gunnar, and Godt, Adelheid. “Trityl Radicals with a Combination of the Orthogonal Functional Groups Ethyne and Carboxyl: Synthesis without a Statistical Step and EPR Characterization”. JOURNAL OF ORGANIC CHEMISTRY 84.6 (2019): 3304-3320.

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