Abstract
THE first serious study of the steric course of this replacement was that of Frankland1, who concluded that phosphorus pentachloride always substitutes with inversion of configuration, whilst thionyl chloride does so except when a phenyl group is attached to the seat of substitution. Although this inference represented a remarkable advance, it is not quite correct, and also requires to be generalized. We have established that all the common substituting agents (PCl5, SOCl2, HCl, PBr5, etc.) produce inversion unless a sufficiently powerful assembly, critical for each reagent, of electron-releasing groups at the seat of substitution reverses this result. For example, such an assembly, effective for all the reagents named, is present in the alcohols CHPhBuα.OH and CHPhBuiso.OH. (We have carried out an improved resolution of the former and a new resolution of the latter.)
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References
J. Chem. Soc., 103, 725 (1913).
ibid., 415 (1930).
Cf. ibid., 382 (1931).
ibid., 463 (1940).
ibid., 218 (1940).
Cowdrey, Hughes, Ingold, Masterman and Scott, ibid., 1252 (1937).
Bateman, Church, Hughes, Ingold and Taher, ibid., 961 et seq. (1940).
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HUGHES, E., INGOLD, C. & WHITFIELD, I. The Walden Inversion in the Replacement of Hydroxyl by Halogen. Nature 147, 206–207 (1941). https://doi.org/10.1038/147206c0
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DOI: https://doi.org/10.1038/147206c0
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