A. Mori, M. Nagayama, H. Mandai
Jun 1, 1971
Citations
0
Influential Citations
16
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
It was shown with a five-membered sultone that the hydrolysis of aliphatic sultones in water proceeds substantially by BAL1-E1 mechanism, and that it is a nucleophilic substitution reaction caused by hydroxyl ion and water. We carried out a kinetic experiment on the hydrolysis of 1,4-butanesultone and ethyl ethanesulfonate, both in water and in water-acetone mixed solvent. It was found that these aliphatic sulfonate esters were hydrolyzed substantially by BAL1-E1 mechanism as in the case of a five-membered sultone, and in particular, ethyl ethanesulfonate was hydrolyzed by complete BAL1-E1 mechanism. The results seem to be justified by a tracer experiment with H218O. Namely, the ratios of the C–O fission to the S–O fission in 1,3-propanesultone and ethyl ethanesulfonate were 85.6:14.4 and 100:0, respectively. In strong alkaline solutions and approtic solvent-water systems, the SN2 reaction involving attack of the nucleophile on sulfur atom took place partly in sultones, but practically not in linear sulfo...