The Study On The New Addition Reaction Of Sulfonylimines

The N-sulfonylimines were prepared by treatment of aromatic aldehydes andp-toluenesulfonamide with titanium tetrachloride. On the basis of this, the additionreactions of N-sulfonylimines with α-bromoketones and α-bromoesters in the presentof zinc powder were carried out. To our knowledge, this addition reaction has neverbeen reported. We have examined the effect of solvent polarity, temperature and timeon the reaction and changed reaction scale, which were taken for the optimizationsystem. Good results were observed. All products are unknown compounds, and theirstructures have been determined by IR, ~1H NMR and element analysis. X-raydiffraction gave the crystal structure of 3-(4-Methoxyphenyl)-1-phenyl-3-(p-toluenesulfonylamino)-1-propanone (MSAP), 3-(3,4-Methylenedioxyphenyl)-1-phenyl-3-(p-toluenesulfonylamino)-1-propanone (MDSAP), 3-(p-Tolyl)-1-phenyl-3-(p-toluenesulfonylamino)-1-propanone (TSAP), 3-(4-Chlorophenyl)-1-phenyl-3-(p-toluenesulfonylamino)-1-propanone (CSAP) in order to elucidate their structure. It was found thatthe four compounds had both the same characteristic and the different things. Thesame characteristic was that two molecules were linked by two intermolecularhydrogen bonds resulting in the formation of a dimer. The difference was that the twointermolecular hydrogen bonds were formed between the amino and carbonyl groupsof two molecules in MSAP and TSAP. But in MDSAP and CSAP, the twointermolecular hydrogen bonds were formed between the amino and sulfonyl groupsof two molecules.A potential mechanism of nucleophilic addition was proposed on the basis of theexperiment data.