| | 1 | Author
| Karin Dölling, Kurt Merzweiler, Christoph Wagner, Horst Weichmann | Requires cookie* | | | Title
| 3-Triorganostannyl-N-diphenylmethylen-alaninestern Synthesis, Structure and Reactivity o f 3-Triorganostannyl-N-diphenylmethylene- alanine Esters  | | | | Abstract
| The deprotonation of N-diphenylmethylene-glycine esters, obtained from glycine ester hy drochlorides and benzophenone imine, and reaction of the resulting carbanions with iodo-methyl triorganostannanes gives the 3-triorganostannyl-N-diphenylmethylene-alanine esters Me2RSnCH2CH(N=CPh2)COOR' (la -e\ R = Me, 'Bu; R' = Me, Et, 'Bu, Bz). These title compounds are transformed into their tin monochlorides MeR(Cl)SnCH2CH(N=CPh2)COOR' (2a -e) by a redistribution reaction with Me2SnCl2. IR and NMR data and the crystal structure of Me2(Cl)SnCH2CH(N=CPh2)COOEt (2b) reveal for 2a -e an intramolecular coordination of the ester C = 0 group at the tin atom. Mild two-phase hydrolysis of la -e with IN HC1 gives the 3-triorganostannyl-alanine ester hydrochlorides Me2RSnCH2CH(NH 2)COOR' • HC1 (3a -e). The transformation of 3a -e into the corresponding alanine esters Me2RSnCH2CH (N H 2)COOR' (4a -e) could be realized with NH3 in chloroform. 4a -e are of limited thermal stability. | | | |
Reference
| Z. Naturforsch. 54b, 293—299 (1999); eingegangen am 10. November 1998 | | | |
Published
| 1999 | | | |
Keywords
| Stannyl Alanine Ester Derivatives, Intramolecular Pentakoordination, NMR Data, Crystal Structure | | | |
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| default:Reihe_B/54/ZNB-1999-54b-0293.pdf | | | | Identifier
| ZNB-1999-54b-0293 | | | | Volume
| 54 | |
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