58534-77-3Relevant academic research and scientific papers
α-Sulfonyl succinimides: Versatile sulfinate donors in Fe-catalyzed, salt-free, neutral allylic substitution
Jegelka, Markus,Plietker, Bernd
, p. 10417 - 10430 (2011/10/31)
Allyl sulfones are versatile intermediates in organic chemistry. The presence of two distinct functional groups sets the stage for a plethora of subsequent transformations. However, despite these advantages the preparation of regioisomerically enriched sulfones is not easy. The use of sulfinate salts as nucleophiles in substitutions is frequently accompanied by side reactions such as π-bond migration, β-elimination, and so on. Herein we present a preparatively simple way to synthesize a variety of different aryl or alkyl allyl sulfones starting from readily accessible allylic carbonates. By employing aryl or alkyl α-sulfonyl succinimides as sulfinate synthons, mild and regioselective ipso substitution of diverse allylic carbonates was realized.
ADDITION REACTION OF SUBSTITUTED BENZENESULFINIC ACIDS TO N-PHENYLMALEIMIDE.
Matsuda,Akiyama,Furuta,Mizuta
, p. 219 - 221 (2007/10/02)
The reaction of substituted benzenesulfinic acids with N-phenylmaleimide has been carried out, and the products obtained have been identified as sulfones from analyses of their IR, UV, and NMR spectra. From the kinetic investigation, a linear Hammett relationship between the sigma -value and log K//2/K//0 has been confirmed. It is concluded that the nucleophilic attack of the sulfinic acid sulfur atom on the carbon of the C equals C bond of N-phenylmaleimide is the rate-determining step.
