Lithium Aluminum Amides: New Reagents for the Synthesis of Imines

References

• Layer , R. W. 1988 . Chem. Rev. , 63 : 489
   Google Scholar
• Stoermer , R. and Von Lepel , F. 1988 . Ber. , 29 : 2110
   Google Scholar
• Henry , L. 1988 . Rec. Trav. Chim. Pays-Bas , 23 : 401
   Google Scholar
• Campbell , K. N. , Sommers , A. H. and Campbell , B. K. 1988 . J. Am. Chem. Soc. , 66 : 82
   Google Scholar
• Tiollais , R. 1988 . Bull. Soc. Chim. Fr. , : 708
   Google Scholar
• Solladié-Cavallo , A. and Bencheqroun , M. 1988 . Tetrahedron Asym. , 2 : 1165
   Google Scholar
• Solladié-Cavallo , A. and Bencheqroun , M. 1988 . J. Org. Chem. , 57 : 5831
   Google Scholar
• 1H-, 13C-NMR and IR spectra of all the imines are consistent with the expected known strucrures : ex.: Imine 10a (C5H11CH═NC3H7) 1H NMR (200 MHz) δppm (CDC13/TMS), 7.54 (1H, tt, J = 5 Hz and 1 Hz, CH═N), 3.23 (2H, td, J = 7 Hz and 1 Hz, CH2-N), 2.15 (2H, td, J = 7 Hz and 5 Hz, CH2-C═N), 1.52 (2H, sext., J = 7 Hz, CH2-CH3 prop.), 1.44 (2H, m, CH2), 1.24 (4H, m, CH2-CH2), ∼0.8 (6H, CH3). Imine 9b (C4H9CH═NCH2Ph) 13C NMR (50 MHz) δ ppm (CDC13/TMS), 165.5 (C═N), 139.5 (C arom.), 128.5, 128.3, 127 (3 CH arom.), 65.2 (N-CH2-Ph), 44.8 (CH2-C═), 26.3 (CH), 22.6 (CH3
   Google Scholar
• The starting aldehydes are easily distinguished from the corresponding imines using the CH═O and CH═N signals, similarly the starting amines are distinguished from the corresponding imines using the CH2-N signals which are deshielded by ∼+0.7ppm in the imines.
   Google Scholar
• No splittings of any signals were noticed in the imines spectra.
   Google Scholar