21288-63-1Relevant academic research and scientific papers
Acid catalyzed alcoholysis of sulfinamides: Unusual stereochemistry, kinetics and a question of mechanism involving sulfurane intermediates and their pseudorotation
Bujnicki, Bogdan,Drabowicz, Jzef,Mikolajczyk, Marian
, p. 2949 - 2972 (2015)
The synthesis of optically active sulfinic acid esters has been accomplished by the acid catalyzed alcoholysis of optically active sulfinamides. Sulfinates are formed in this reaction with a full or predominant inversion of configuration at chiral sulfur or with predominant retention of configuration. The steric course of the reaction depends mainly on the size of the dialkylamido group in the sulfinamides and of the alcohols used as nucleophilic reagents. It has been found that bulky reaction components preferentially form sulfinates with retention of configuration. It has been demonstrated that the stereochemical outcome of the reaction can be changed from inversion to retention and vice versa by adding inorganic salts to the acidic reaction medium. The unusual stereochemistry of this typical bimolecular nucleophilic substitution reaction, as confirmed by kinetic measurements, has been rationalized in terms of the addition-elimination mechanism, A-E, involving sulfuranes as intermediates which undergo pseudorotations.
The sulfinyl moiety in Lewis base-promoted allylations
Fulton, J. Robin,Kamara, Lamin M.,Morton, Simon C.,Rowlands, Gareth J.
experimental part, p. 9134 - 9141 (2010/01/06)
By employing Senanayake's oxathiazolidine-2-oxide reagent, a collection of sulfinamides was prepared and provided the first examples of sulfinamides promoting the allylation of benzaldehyde and N-benzoylhydrazones with allyltrichlorosilane. The optimum su
