35034-65-2Relevant academic research and scientific papers
Palladium-catalyzed aromatic sulfonylation: A new catalytic domino process exploiting in situ generated sulfinate anions
Le Duc, Ga?tan,Bernoud, Elise,Prestat, Guillaume,Cacchi, Sandro,Fabrizi, Giancarlo,Iazzetti, Antonia,Madec, David,Poli, Giovanni
, p. 2943 - 2946 (2011)
Allylic sulfones are excellent precursors of aryl sulfones via a new Pd-catalyzed domino sequence involving in situ generation of sulfinate anions and subsequent cross-coupling with aryl -iodides or bromides. Georg Thieme Verlag Stuttgart · New York.
A KINETIC STUDY OF THE FRIEDEL-CRAFTS REACTION OF NAPHTHALENE WITH PARA- SUBSTITUTED BENZENESULPHONYL CHLORIDES: THE EFFECT OF THE SUBSTITUENT
Yoshii, Yoshihiro,Ito, Akiyoshi,Hirashima, Tsuneaki,Shinkai, Seiji,Manabe, Osamu
, p. 777 - 782 (2007/10/02)
The kinetics of the Friedel-Crafts reaction of naphthalene with para-substituted benzenesulphonyl chlorides have been investigated.The rate constants for equations (i) (formation of the sulphonyl cation) and (ii) (sulphone formation) were determined separately.The effect of the para-substituents on k1 was XC6H4SO2Cl + AlCl3 XC6H4SO2+*AlCl4- , XC6H4SO24*AlCl4- + C10H8 XC6H4SO2C10H7*AlCl3 + HCl well expressed by Yukawa-Tsuno equation, log(k1X/K1H)= ρ1(Δ?R(+))> where ρ1= -2.7 and γ1= 0.4.On the other hand, the effect of the para-substituents on k3(=k1k2/k-1) was expressed by the Brown-Okamoto equation, log(k3X/k3H)= ρ3?+ where ρ3= -2.8.Thus, the electron-donating para-substituents gave the greater reaction rates.We concluded that the sulphonyl cation gives large negative ρ values as a result of its high reactivity, and that its low selectivity for α-attack is due to a steric effect.These kinetic results have been rationalised in terms of bifunctional acid-base catalysis in phenylsulphonnylation.
