Regio- and stereoselective lithiation of 2,3-diphenylaziridines: a multinuclear NMR investigation.
The alpha-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 cis-1-Li in THF and dimeric trans-1-Li in toluene) are involved.
Capriati
Vito
V
Dipartimento Farmaco-Chimico, Università di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi CINMPIS, Via E. Orabona 4, I-70125 - Bari, Italy.
Florio
Saverio
S
Luisi
Renzo
R
Mazzanti
Andrea
A
Musio
Biagia
B
D001388:Aziridines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature; D014050:Toluene / Q000737:chemistry
D001388:Aziridines; D014050:Toluene; D008094:Lithium