The invention of new radical chain reactions. Part 11. A new method for the generation of tertiary radicals from tertiary alcohols
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1603-1611
- https://doi.org/10.1039/p19860001603
Abstract
A convenient procedure for the radical deoxygenation of tertiary alcohols has been invented using the double half esters of oxalic acid with the t-alcohol and N-hydroxypyridine-2-thione. Decomposition of this type of ester in the presence of 1,1-dimethylethane- or (better) 1,1-diethylpropane-thiol gave the corresponding hydrocarbons in good yield. It has been shown that the oxalate fragmentation is not concerted, but involves a stepwise loss of carbon dioxide. Tertiary alcohols are also a convenient source of radicals for addition to suitable alkenes with formation of quaternary centres.Keywords
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