Solution Structure and Chelation Properties of 2-Thienyllithium Reagents

The solution and chelation properties of 2-thienyllithium reagents with potential amine and ether chelating groups in the 3-position and related model systems have been investigated using low temperature 6Li, 7Li, 13C, and 31P NMR spectroscopy, 15N-labeling, and the effect of solvent additives. In T...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-09, Vol.70 (19), p.7520-7529
Main Authors: Jantzi, Kevin L, Puckett, Craig L, Guzei, Ilia A, Reich, Hans J
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:The solution and chelation properties of 2-thienyllithium reagents with potential amine and ether chelating groups in the 3-position and related model systems have been investigated using low temperature 6Li, 7Li, 13C, and 31P NMR spectroscopy, 15N-labeling, and the effect of solvent additives. In THF−ether mixtures at low temperature 3-(N,N-dimethylaminomethyl)-2-thienyllithium (4) is ca. 99% dimer (which is chelated) and 1% monomer (unchelated), whereas 3-(methoxymethyl)-2-thienyllithium (5) is
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050592+