Structural studies of {Li-6} 2-lithiopyrrolidines using NMR spectroscopy

by Gawley, Robert E.; Klein, Rosalyn; Ashweek, Neil J.; Coldham, Iain

A selection of N-substituted 2-lithiopyrrolidines were prepared and their structures were investigated by Li-6 and C-13 NMR spectroscopy. Evidence is presented for aggregation and dynamic solvation effects, depending on the nature of the N-substituent and substituents on the pyrrolidine ring. Studies were performed with N-Boc (coordinating carbonyl group), N-methoxyethyl (coordinating methoxy group) and N-alkyl (no coordinating group) heterocycles to represent three different classes of organolithiums: dipole-stabilized, unstabilized and chelated, and unstabilized. (c) 2005 Elsevier Ltd. All rights reserved.

Journal
Tetrahedron
Volume
61
Issue
13
Year
2005
Start Page
3271
ISBN/ISSN
1464-5416; 0040-4020
DOI
10.1016/j.tet.2005.01.098