The R-lithiation-trapping sequence of trans-N-alkyl-2,3-diphenylaziridines (s-BuLi or s-BuLi/TMEDA), taking place with a stereochemistry which dramatically depends on the solvent coordinating ability (inversion of configuration in THF and retention in toluene), has been carefully investigated. 1H,13C, and 7Li multinuclear NMR investigations at low temperature suggest that two differently configured lithiated aziridines (monomeric is-1-Li in THF and dimeric trans-1-Li in toluene) are involved.
V. Capriati, S. Florio, R. Luisi, A. Mazzanti, B. Busio (2008). Regio- and Stereoselective Lithiation of 2,3- Diphenylaziridines: A Multinuclear NMR Investigation. JOURNAL OF ORGANIC CHEMISTRY, 73, 3197-3204 [10.1021/jo800069k].
Regio- and Stereoselective Lithiation of 2,3- Diphenylaziridines: A Multinuclear NMR Investigation
MAZZANTI, ANDREA;
2008
Abstract
The R-lithiation-trapping sequence of trans-N-alkyl-2,3-diphenylaziridines (s-BuLi or s-BuLi/TMEDA), taking place with a stereochemistry which dramatically depends on the solvent coordinating ability (inversion of configuration in THF and retention in toluene), has been carefully investigated. 1H,13C, and 7Li multinuclear NMR investigations at low temperature suggest that two differently configured lithiated aziridines (monomeric is-1-Li in THF and dimeric trans-1-Li in toluene) are involved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
