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Reaction of Halogen Compounds on DisodioSuccinosuccinic Ester. II. Further Notes on the Reaction with Iodoacetic Ester
Author(s) -
Chang Daniel Y.,
Liu TienChih,
Wei YunTsung,
Kung WenShen,
Sun WenKim
Publication year - 1960
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.196000013
Subject(s) - chemistry , iodoacetic acid , halogen , cyclohexane , molecule , organic chemistry , iodide , iodine , infrared spectroscopy , stereospecificity , acetic acid , medicinal chemistry , catalysis , alkyl , enzyme
Additional evidences have been found to support the view that two of the crystalline products resulting from the reaction between iodoacetic ester and disodiosuccinosuccinic ester, those with melting points 106°, and 60°, consisted of stereoisomers. In the first place, the infrared spectra of both substances bear close resemblance Secondly, the keto acids that were obtained by ketonic cleavage of these substances could be converted into identical products and, when reduced by the Wolff‐Kishner method modified by Huang Minlon, they furnished the same cyclohexane‐1, 4‐bis‐[acetic acid]. The determination of the molar polarization of the crystalline substances at different temperatures showed that neither the substance with m. p. 106° nor that with m. p. 60° had a center of symmetry in its molecule. These substances also had almost equal dipole moments. These results are briefly discussed. The decomposition reactions of the substances with m. p. 106° and 60° when heated with sodium iodide have been found to be a general reaction characteristic of β‐ketonic esters.