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
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 12,p. 1821-1827
- https://doi.org/10.1039/p29800001821
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.Keywords
This publication has 0 references indexed in Scilit: