224964-22-1Relevant academic research and scientific papers
Synthesis, Structure and Reactivity of 3-Triorganostannyl-N-diphenylmethylene-alanine Esters
Doelling, Karin,Merzweiler, Kurt,Wagner, Christoph,Weichmann, Horst
, p. 293 - 299 (2007/10/03)
The deprotonation of N-diphenylmethylene-glycine esters, obtained from glycine ester hydrochlorides and benzophenone imine, and reaction of the resulting carbanions with iodomethyl triorganostannanes gives the 3-triorganostannyl-N-diphenylmethylene-alanine esters Me2RSnCH2CH(N=CPh2)COOR1 (1a - e; R = Me, 1Bu; R1 = Me, Et, 1Bu, Bz). These title compounds are transformed into their tin monochlorides MeR(Cl)SnCH2CH(N=CPh2)COOR1 (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=O group at the tin atom. Mild two-phase hydrolysis of 1a - e with 1N HCl gives the 3-triorganostannyl-alanine ester hydrochlorides Me2RSnCH2CH(NH2)COOR1 · HCl (3a - e). The transformation of 3a - e into the corresponding alanine esters Me2RSnCH2CH(NH2)COOR1 (4a - e) could be realized with NH3 in chloroform. 4a - e are of limited thermal stability.
