title: Isomerization of Trimethyl alpha-Keto Trithioorthocarboxylates into alpha,alpha-Bis(methylthio) Thiolcarboxylates. A New Rearrangement of Synthetic Interest.
abstract: A study was made of the isomerization reaction of a great variety of trimethyl alpha-keto trithioorthocarboxylates to alpha,alpha-bis(methylthio) thiolcarboxylates, intermediates of high synthetic value for the synthesis of alpha-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.
authors.affiliation: Dipartimento di Chimica Generale ed Organica Applicata dell'Università, C.so M. D'Azeglio 48, I-10125 Torino, Italy.
authors.forename: Iacopo
authors.initials: I
authors.lastname: Degani
authors.forename: Stefano
authors.initials: S
authors.lastname: Dughera
authors.forename: Rita
authors.initials: R
authors.lastname: Fochi
authors.forename: Sonia
authors.initials: S
authors.lastname: Gazzetto