39149-63-8Relevant academic research and scientific papers
Preparation of N-aryl-S,S-diphenylsulfilimines by nucleophilic attack of N-lithio-S,S-diphenylsulfilimine on aromatic compounds
Claridge, Robert P.,Millar, Ross W.,Sandall, John P. B.,Thompson, Claire
, p. 10243 - 10252 (1999)
N-Aryl-S,S-diphenylsulfilimines with unusual substitution patterns have been prepared by reacting the novel nitrogen nucleophile N-lithio-S,S- diphenylsulfilimine with a range of activated aromatic substrates. N-lithio- S,S-diphenylsulfilimine is not only able to displace chloro groups in conventional aromatic nucleophilic substitution reactions, but also, unlike S,S-diphenylsulfilimine itself, can attack at hydrogen-bearing positions in 'vicarious' aromatic nucleophilic substitutions of hydrogen.
Kinetics and mechanism of the reaction of S,S-diphenylsulfilimine with a series of aryl halides
Sandall, John P. B.,Thompson, Claire,Steel, Nicholas J. D.
, p. 513 - 516 (2007/10/03)
The stoichiometry, rate constants and order of reaction have been determined for the reaction of S,S-diphenylsulfilimine with the substrates 1-fluoro-2,4-dinitrobenzene, 1-chloro-2,4-dinitrobenzene, 2-chloro-3-nitropyridine, 2-chloro-5-nitropyridine and 2-chloro-3,5-dinitropyridine. Arrhenius parameters and solvent effects have also been determined for some of these reactions. The results demonstrate that the reaction is a typical nucleophilic aromatic substitution process with no measurable base catalysis. A high reactivity of the sulfilimine reagent is observed and accounted for in terms of the contribution of the ylid form to the overall structure.
