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By James Morrison (Eds.)
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Extra info for Asymmetric Synthesis
Pirkle, W. , and Beare, S. D. (1967). J. Am. Chem. Soc 89, 5485. Plattner, PI. , and Heusser, H. (1944). Helv. Chim. Acta 27, 748. Schipper, P. E. (1975). Inorg. Chim. Acta 12, 199. Schwarz, J. C. P. (1964). In "Physical Methods in Organic Chemistry" (J. C. P. ), pp. 2 3 5 - 2 4 3 . Holden-Day, San Francisco. Snatzke, G. (1967). In "Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry" (G. ), pp. 3 3 5 - 3 4 0 . Heyden & Son, London. Tanford, C. (1962). J. Am. Chem. Soc. 84, 1747.
Soc. 80, 465. , and Horeau, A. (1977a). Tetrahedron 3 3 , 245. , and Horeau, A. (1977b). , p. 3259. 4 Isotope-Dilution Techniques Kenneth K. Andersen Diana M. Gash John D. Robertson Department o f Chemistry University of N e w Hampshire D u r h a m , N e w Hampshire I. II. III. IV. V. Introduction History Theory Errors Examples References 45 46 47 52 53 57 I. Introduction The method of isotope dilution can be used to determine the enantiomeric excess (ee) of a sample. This technique proceeds as described on the following page: 1 'There has been some debate (Valentine and Scott, 1978) about how best to express the ratios of enantiomers in mixtures.
6% of its original value (Fig. 6). Experimentally, a value of 572 counts per minute per milligram was obtained for the recrystallized sample. This demonstrated that natural caldariomycin constituted half of the synthetic racemate. Kemp et al. (1970) used the principle of isotope dilution in preparing an isotopically labeled chiral substance containing negligible label in any con taminating enantiomer. This was accomplished by successive dilution of a la beled enantiomer of high enantiomeric purity with a small quantity of unlabeled racemate.