Free radical reactions in solution. Part 4. Radical-initiated reduction of acid chlorides to alkanes by tri-n-propylsilane: removal of unwanted carboxy-groups from organic molecules
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1137-1141
- https://doi.org/10.1039/p19790001137
Abstract
Aliphatic acyl chlorides RCOCl react with tripropylsilane in the presence of t-butyl peroxide at 140–170° to give the corresponding alkane RH. Yields are good when R is a primary or secondary alkyl group, poor when R is tertiary or benzylic, and zero when R is phenyl. A radical chain reaction is postulated. The reaction should be synthetically useful for removing carboxy-groups from carboxylic acids RCO2H, where R is a primary or secondary alkyl group.Keywords
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