Acid Catalyzed Alcoholysis of Sulfinamides: Unusual Stereochemistry, Kinetics and a Question of Mechanism Involving Sulfurane Intermediates and Their Pseudorotation

Acid Catalyzed Alcoholysis of Sulfinamides: Unusual Stereochemistry, Kinetics and a Question of Mechanism Involving Sulfurane Intermediates and Their Pseudorotation

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 configuratio...

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Bibliographic Details
Main Authors: Bogdan Bujnicki, Józef Drabowicz, Marian Mikołajczyk
Format: Article
Language:English
Published: MDPI AG 2015-02-01
Series:Molecules
Subjects:
sulfur chirality
stereoselective synthesis
chiral sulfinamides
chiral sulfinates
enantiomer interconversion
nucleophilic substitution
addition-elimination mechanism
sulfuranes
pseudorotation
Online Access:http://www.mdpi.com/1420-3049/20/2/2949

Internet

http://www.mdpi.com/1420-3049/20/2/2949

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