Free-radical substitution in aliphatic compounds. Part XV. The chlorination of butyl methyl ether and dibutyl ether

Abstract

The photochemical chlorination of ethers is shown to result in predominant attack at the carbon atoms to which the ether oxygen is attached. The resultant radical is unstable and in the gas phase breaks down to yield an alkyl radical and an aldehyde. Assuming that attack at the α-positions yields the aldehyde quantitatively, we calculated values for relative rates of attack RS_p^x in butyl methyl ether.