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

…, B Ortiz, R Sánchez-Obregón, A Fraile…

Index: Yuste, Francisco; Hernandez Linares, Angelica; Mastranzo, Virginia M.; Ortiz, Benjamin; Sanchez-Obregon, Ruben; Fraile, Alberto; Garcia Ruano, Jose Luis Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4635 - 4644

Full Text: HTML

Citation Number: 11

Abstract

The Friedel–Crafts reaction of methyl alkyl-and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NHR, NR2), 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 ...