Free radical substitution. Part 34. The chlorination of 1- and 2-nitrobutanes in the gas and liquid phases

Abstract

1- and 2-nitrobutanes have been chlorinated in the gas phase and in solution. The intermediate nitrobutyl radicals with the nitro-group in a β-position are unstable and in the gas phase lose NO₂ to yield the corresponding butene. The relative rates of attack at the various sites have been determined. The nitro-group proves to be the most deactivating non-ionic substituent studied so far.