An electron spin resonance study of the reactions of organosilicon, organogermanium, and organotin radicals with carbonyl compounds
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 14,p. 1933-1937
- https://doi.org/10.1039/p29730001933
Abstract
Addition of organosilyl, organogermyl, organotin, and organolead radicals to the oxygen atom of carbonyl compounds has been investigated by e.s.r. spectroscopy. Ease of addition, to a given carbonyl compound, falls in the order R3Si· > R3Ge·∼ R3Sn· > R3Pb·, and for a given Group IVB radical, diketones > oxalates > ketones > trifluoroacetates > formates > acetates. The results are rationalized in terms of bond energy differnces, stabilization of radicals formed, and polar effects. Tris(trimethylsilyl)silyl is less reactive than triethylsilyl. Organotin radicals react with α-diketones, oxalates, to give spectra which are best interpreted as being due to radical anions.Keywords
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