Oxymetallation. Part III. Competitive epoxidation during the hydridodemercuration of β-mercurated dialkyl peroxides with sodium borohydride
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2433-2438
- https://doi.org/10.1039/p19720002433
Abstract
Reduction by sodium borohydride of the compounds R1R2C(OOBut) CH2·HgX, which are formed by t-butyl-peroxymercuration of terminal alkenes, leads to the formation of epoxides, R1R2[graphic omitted], in addition to the expected dialkyl peroxides, R1R2C(OOBut)Me. The amount of epoxidation increases with increasing alkylation in the terminal alkene and with the temperature at which the reduction is carried out. It is suggested that the results are consistent with homolytic cleavage of the carbon-mercury bond during demercuration.Keywords
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