Reactions of 2,3-dibromopropan-1-ol and 1,3-dichloropropan-2-ol with elemental sulfur activated in the system hydrazine hydrate-2-aminoethanol at 30-35°C gave oligomeric polysulfides which were subjected to reductive cleavage with formation of individual dithioglycerol isomers. Activation of sulfur with the use of alkali gives rise to mixtures of isomeric products.
Activation Parameters for Thiolate-Disulfide Interchange Reactions in Aqueous Solution
We have measured activation parameters for thiolate-disulfide interchange reactions in water.Two disulfides were examined (Ellman's reagent and oxidized glutathione) and three thiols (2-mercaptoethanol, 1,3-dithiopropan-2-ol, and 1,4-dithiothreitol).These values are consistent with the interpretation of this reaction as an uncomplicated SN2 reaction of thiolate anion on the disulfide bond.
Whitesides, George M.,Houk, Janette,Patterson, Mark A. K.
p. 112 - 115
(2007/10/02)
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