Iminodiacetate as a didentate ligand: base induced dealkylation

作者: Richard M. Hartshorn

DOI: 10.1039/B203597A

关键词: AlkylationGlycineAmino acidChemistryStereochemistryChelationMedicinal chemistryLigandBase (chemistry)Reaction conditionsImine

摘要: Iminodiacetate has been incorporated into a complex as didentate ligand. Control of pH is vital to the successful synthesis complex. At > 8 glycinato complexes have observed be significant products from synthesis. Evidence presented in support proposal that glycine results oxidative dealkylation coordinated iminodiacetate. An imine similar possible intermediate this reaction prepared and shown give rise amino acid on submission conditions. The are formed derived either pendant or chelated parts Possible mechanisms discussed.

参考文章(16)
Dennis P. Riley, Donald L. Fields, Willie Rivers, Homogeneous catalysts for selective molecular oxygen driven oxidative decarboxylations Journal of the American Chemical Society. ,vol. 113, pp. 3371- 3378 ,(1991) , 10.1021/JA00009A023
W. G. Jackson, A. M. Sargeson, Rate of inversion of sulfur in cobalt(III)-thioether complexes Inorganic Chemistry. ,vol. 17, pp. 2165- 2169 ,(1978) , 10.1021/IC50186A027
Takahiko Kojima, Junichi Tsuchiya, Satoru Nakashima, Hiroaki Ohya-Nishiguchi, Shigenobu Yano, Masanobu Hidai, Observation of radical intermediates for unusual carbon-nitrogen bond formation of .alpha.-aminomalonate to give an .alpha.-diamine linkage. ESR studies on electron transfer reactions in cobalt(III)-polyamine complexes Inorganic Chemistry. ,vol. 31, pp. 2333- 2340 ,(1992) , 10.1021/IC00038A009
K. O. Hiller, K. D. Asmus, Formation and reduction reactions of .alpha.-amino radicals derived from methionine and its derivatives in aqueous solutions The Journal of Physical Chemistry. ,vol. 87, pp. 3682- 3688 ,(1983) , 10.1021/J100242A022
Motoshichi Mori, Muraji Shibata, Eishin Kyuno, Fukun Maruyama, The Cobalt(III) Complexes of Ethylenediaminediacetic and Ammoniadiacetic Acids Bulletin of the Chemical Society of Japan. ,vol. 35, pp. 75- 77 ,(1962) , 10.1246/BCSJ.35.75
T. Kojima, T. Usui, A. Shimada, M. Yashiro, T. Tanase, R. Yoshioka, R. Kuroda, S. Yano, M. Hidai, . et al., Syntheses and characterization of complexes derived from .alpha.-aminomalonate and trans-[CoCl2(2,3,2-tet)]+ (2,3,2-tet = 1,9-diamino-3,7-diazanonane) Inorganic Chemistry. ,vol. 30, pp. 4535- 4541 ,(1991) , 10.1021/IC00024A014
David A. Buckingham, Ian Stewart, Paul A. Sutton, Proton exchange and epimerization of cobalt(III) chelated amino acids via carbanion intermediates Journal of the American Chemical Society. ,vol. 112, pp. 845- 854 ,(1990) , 10.1021/JA00158A053
E. K. Chong, J. MacB. Harrowfield, W. G. Jackson, Alan M. Sargeson, J. Springborg, Metal ion promoted elimination reactions. Conversion of .beta.-hydroxy .alpha.-amino acids to .alpha.-imino acids Journal of the American Chemical Society. ,vol. 107, pp. 2015- 2022 ,(1985) , 10.1021/JA00293A036
Motowo Yamaguchi, Masahiko Saburi, Sadao Yoshikawa, Novel oxidative dehydrogenation reaction of .alpha.-amino acids chelated to cobalt(III) ion: synthesis of (2-iminocarboxylato)cobalt(III) complexes Journal of the American Chemical Society. ,vol. 106, pp. 8293- 8295 ,(1984) , 10.1021/JA00338A048