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

The Journal of Organic Chemistry
Henrik HintzAdelheid Godt

Abstract

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 T1 and T2 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 impr...Continue Reading

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Citations

Dec 19, 2019·Chemistry : a European Journal·Victor M TormyshevElena G Bagryanskaya
Jan 1, 2019·RSC Advances·Martin PonceletBenoit Driesschaert
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Jan 7, 2021·Chemistry : a European Journal·Nico FleckOlav Schiemann
May 12, 2021·Journal of the American Chemical Society·Youngsuk KimEunsung Lee
May 28, 2021·The Journal of Organic Chemistry·Li ChenYangping Liu
Oct 28, 2020·The Journal of Organic Chemistry·Thanh Binh NguyenPascal Retailleau
Jul 24, 2020·The Journal of Organic Chemistry·Urikhan SanzhaevaBenoit Driesschaert

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