100396-92-7Relevant academic research and scientific papers
Preparation of (phenylsulfinyl)phenols from aryl phenylsulfinates: 'Thia-Fries rearrangement'
Jung, Michael E.,Lazarova, Tsvetelina I.
, p. 7 - 8 (1996)
Treatment of aryl phenylsulfinates 5 (prepared from phenols 1 by reaction with phenylsulfinyl chloride) with AlCl3 at 25°C furnishes good yields of the (phenylsulfinyl)phenols 2 via a 'thia-Fries rearrangement'.
Methyl sulfinates as electrophiles in friedel-crafts reactions. Synthesis of aryl sulfoxides
Yuste, Francisco,Hernandez Linares, Angelica,Mastranzo, Virginia M.,Ortiz, Benjamin,Sanchez-Obregon, Ruben,Fraile, Alberto,Garcia Ruano, Jose Luis
, p. 4635 - 4644 (2011/07/29)
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 steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.
