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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Methyl sulfinates as electrophiles in Friedel-Crafts reactions. Synthesis of aryl sulfoxides
Francisco Yuste1, Angélica Hernández Linares, Virginia M Mastranzo
1Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, México D F. yustef@unam.mx
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.
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