Bis-Spiro-Oxetane and Bis-Spiro-Tetrahydrofuran Pyrroline Nitroxide Radicals: Synthesis and Electron Spin Relaxation Studies

Autor:	Shengdian Huang, Suchada Rajca, Gareth R. Eaton, Thacien Ngendahimana, Andrzej Rajca, Sandra S. Eaton, Maren Pink
Rok vydání:	2021
Předmět:	Nitroxide mediated radical polymerization Hydrogen bond Radical Organic Chemistry Relaxation (NMR) Electron Spin Resonance Spectroscopy Electrons Pyrroline Oxetane Trehalose chemistry.chemical_compound chemistry Ethers Cyclic Polymer chemistry Nitrogen Oxides Pyrroles Furans Tetrahydrofuran
Zdroj:	The Journal of Organic Chemistry. 86:13636-13643
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c01670
Popis:	Synthesis of bis-spiro-oxetane and bis-spiro-tetrahydrofuran pyrroline nitroxide radicals relies on the Mitsunobu reaction-mediated double cyclizations of N-Boc protected pyrroline tetraols. Structures of the nitroxide radicals are supported by X-ray crystallography. In a trehalose/sucrose matrix at room temperature, the bis-spiro-oxetane nitroxide radical possesses electron spin coherence time, Tm ≈ 0.7 μs. The observed enhanced Tm is most likely associated with strong hydrogen bonding of oxetane moieties to the trehalose/sucrose matrix.
Databáze:	OpenAIRE
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