AN UNUSUAL REARRANGEMENT LEADING TO ORTHO-THIOMETHYLATION OF ARYLACETIC ACID-DERIVATIVES

Citation
M. Bourgaux et al., AN UNUSUAL REARRANGEMENT LEADING TO ORTHO-THIOMETHYLATION OF ARYLACETIC ACID-DERIVATIVES, Synlett, (1), 1995, pp. 113-115
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
09365214
Issue
1
Year of publication
1995
Pages
113 - 115
Database
ISI
SICI code
0936-5214(1995):1<113:AURLTO>2.0.ZU;2-C
Abstract
Arylacetic esters 1 are converted into the corresponding ketene acetal s 2 by O-silylation. Compounds 2 smoothly rearrange in refluxing THF t o give the ortho-thiomethylated arylacetic acids 4 after hydrolysis. T he sequence can be performed with good yields (63-81%) as a one-pot pr ocess.