53876-79-2Relevant academic research and scientific papers
Hypervalent iodine compounds for anti-markovnikov-type iodo-oxyimidation of vinylarenes
Krylov, Igor B.,Paveliev, Stanislav A.,Syroeshkin, Mikhail A.,Korlyukov, Alexander A.,Dorovatovskii, Pavel V.,Zubavichus, Yan V.,Nikishin, Gennady I.,Terent’ev, Alexander O.
, p. 2146 - 2155 (2018)
The iodo-oxyimidation of styrenes with the N-hydroxyimide/I2/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc)2 proved to be the most effective; yields of iodo-oxyimides are 34–91%. A plausible reaction pathway includes the addition of an imide-N-oxyl radical to the double C=C bond and trapping of the resultant benzylic radical by iodine. It was shown that the iodine atom in the prepared iodo-oxyimides can be substituted by various nucleophiles.
NUCLEOPHILIC ADDITION TO STYRYL SULPHONES. PART I. A STUDY ON THE REGIOCHEMISTRY.
Benedetti, F.,Fabrissin, S.,Risaliti, A.
, p. 3887 - 3894 (2007/10/02)
Styryl sulphones undergo nucleophilic addition, with the nucleophile adding at the α- or the β-position, with respect to the sulphone group; β-attack is normally favoured over α-attack.Factors which can change the regioselectivity in favour of the addition of the nucleophile to the α-position are discussed for heteronucleophiles as well as carbon nucleophiles.
