Peroxides of elements other than carbon. Part XVII. The reaction of trialkylstibines and trialkylbismuthines with t-butyl hydroperoxide and with oxygen
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 1660-1665
- https://doi.org/10.1039/j39710001660
Abstract
T-Butyl hydroperoxide reacts with trialkylstibines, R3M, to give the corresponding stibine oxides, R3MO, but with trialkylbismuthines to give products such as RO·OBut, ROH, and ROR. Both reactions are thought to involve the intermediate metallonium ion R3MOH, which undergoes nucleophilic attack on H when M = Sb, and on R when M = Bi. The autoxidation of the stibines and bismuthines involves a radical chain reaction, and gives products similar to those obtained with t-butyl hydroperoxide. It is suggested that an alkylperoxymetallic compound, R2MO·OR, is formed by homolytic alkylperoxydealkylation at the metal, followed by reduction of the peroxide by R3M.Keywords
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