Issue 12, 1980

The selectivity of attack by the hydroxyl radical on myoinositol, and the importance of stereoelectronic factors upon radical rearrangement: an electron spin resonance conformational-analysis study

Abstract

E.s.r. spectroscopy has been employed to show that the reaction of ·OH with the model substrate myoinositol is unselective; at pH 4, e.s.r. signals of all possible radicals produced by C–H abstraction are detected. A conformational analysis based on the hyperfine splittings is presented. The rates of acid-catalysed rearrangement of the radicals have been measured; the radical with an axial β-hydroxy-group is shown to lose water with a rate constant (ca. 3 × 106 dm3 mol–1 s–1) which is considerably greater than those of the radicals with only equatorial β-hydroxy-groups. This is interpreted in terms of a significant stereoelectronic requirement for rearrangement.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1980, 1821-1827

The selectivity of attack by the hydroxyl radical on myoinositol, and the importance of stereoelectronic factors upon radical rearrangement: an electron spin resonance conformational-analysis study

B. C. Gilbert, D. M. King and C. B. Thomas, J. Chem. Soc., Perkin Trans. 2, 1980, 1821 DOI: 10.1039/P29800001821

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