Regio- and stereoselective lithiation of 2,3-diphenylaziridines: A multinuclear NMR investigation

被引:36
作者
Capriati, Vito [1 ]
Florio, Saverio [1 ]
Luisi, Renzo [1 ]
Mazzanti, Andrea [2 ]
Musio, Biagia [1 ]
机构
[1] Univ Bari, Dipartimento Farmacochim, CINMPIS, I-70125 Bari, Italy
[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
关键词
D O I
10.1021/jo800069k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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. H-1,C-13, and Li-7 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.
引用
收藏
页码:3197 / 3204
页数:8
相关论文
共 37 条
[1]   Solid-state C-13-NMR-spectroscopic investigations of alpha-(dimethylamino)-benzyllithium complexes [J].
Ahlbrecht, H ;
Harbach, J ;
Kalinowski, HO ;
Lang, A ;
Maier, G .
CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (06) :683-686
[2]   STRUCTURE OF ALPHA-(DIMETHYLAMINO)BENZYLLITHIUM IN SOLUTION - DYNAMIC EQUILIBRIUM BETWEEN AN ETA-1 AND AN ETA-3 SPECIES [J].
AHLBRECHT, H ;
HARBACH, J ;
HAUCK, T ;
KALINOWSKI, HO .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (07) :1753-1762
[3]  
AHLBRECHT H, 1995, LIEBIGS ANN, P211
[4]   Modified, pulse field gradient-enhanced inverse-detected HOESY pulse sequence for reduction of t1 spectral artifacts [J].
Alam, TM ;
Pedrotty, DM ;
Boyle, TJ .
MAGNETIC RESONANCE IN CHEMISTRY, 2002, 40 (05) :361-365
[5]  
Bauer W, 1996, MAGN RESON CHEM, V34, P532
[6]  
Bauer W., 1995, LITHIUM CHEM THEORET, P125
[7]  
BINSCH G, 1978, ANGEW CHEM INT EDIT, V10, P570
[8]  
Boche G., 1995, LITHIUM CHEM, P195
[9]   STEREOELECTRONIC EFFECTS ON THE STABILITIES OF ANIONS AND RADICALS DERIVED FROM 2-BENZOYLPERHYDROPYRIMIDINES [J].
BORDWELL, FG ;
VANIER, NR ;
ZHANG, XM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9856-9857
[10]   IS N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE A GOOD LIGAND FOR LITHIUM [J].
COLLUM, DB .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (10) :448-454