title: Methyl sulfinates as electrophiles in Friedel-Crafts reactions. Synthesis of aryl sulfoxides.
abstract: 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.
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, México D F. yustef@unam.mx
authors.forename: Francisco
authors.initials: F
authors.lastname: Yuste
authors.forename: Angélica Hernández
authors.initials: AH
authors.lastname: Linares
authors.forename: Virginia M
authors.initials: VM
authors.lastname: Mastranzo
authors.forename: Benjamín
authors.initials: B
authors.lastname: Ortiz
authors.forename: Rubén
authors.initials: R
authors.lastname: Sánchez-Obregón
authors.forename: Alberto
authors.initials: A
authors.lastname: Fraile
authors.forename: José Luis García
authors.initials: JL
authors.lastname: Ruano