Methyl Sulfinates as Electrophiles in Friedel–Crafts Reactions. Synthesis of Aryl Sulfoxides

Autor: Francisco Yuste, Alberto Fraile, Rubén Sánchez-Obregón, Virginia M. Mastranzo, Angélica Hernández Linares, Benjamín Ortiz, José L. García Ruano
Rok vydání: 2011
Předmět:
Zdroj: The Journal of Organic Chemistry. 76:4635-4644
ISSN: 1520-6904
0022-3263
DOI: 10.1021/jo2006335
Popis: The Friedel-Crafts reaction of methyl alkyl- and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NHR, NR(2)), provides alkyl aryl and diaryl sulfoxides under mild conditions and in moderate to good yields. The very high regioselectivity usually observed in these sulfinylation reactions is rationalized on the basis of a Wheland intermediate having a trigonal bypyramidal structure in which steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.
Databáze: OpenAIRE