Isomerization of Trimethyl α-Keto Trithioorthocarboxylates into α,α-Bis(methylthio) Thiolcarboxylates. A New Rearrangement of Synthetic Interest
A study was made of the isomerization reaction of a great variety of trimethyl α-keto trithioorthocarboxylates to α,α-bis(methylthio) thiolcarboxylates, intermediates of high synthetic value for the synthesis of α-arylpropionic acids. The reaction was carried out in methylene chloride in the presence of catalytic amounts of trityl perchlorate or methanesulfonic acid and was complete in 2 h at rt. In most of the investigated cases the result was positive, the yields usually being greater than 90%. Also the reaction mechanism was subjected to an experimental study.
Synthesis of Disulfides from the Palladium(0)-Catalyzed Reactions of Sulfenyl Halides and Organostannanes
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Cochran, John C.,Friedman, Susan R.,Frazier, John P.
p. 1533 - 1536
(2007/10/03)
On the Mechanism of the Cleavage Reaction of (Methylthio)methyl Ether with Triphenylmethyl Cation
The cleavage reaction of a (methylthio)methyl (MTM) ether with triphenylmethyl cation was not initiated by the previously proposed hydride abstraction with triphenylmethyl cation but promoted by the coordination of triphenylmethyl cation as a Lewis acid to the sulfur atom in the MTM group.
Niwa, Haruki,Miyachi, Yasuyoshi
p. 716 - 718
(2007/10/02)
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