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Reference

Friedel-Crafts phenylsulfonylation of o-xylene, indan, and tetralin in nitrobenzene

Friedel-Crafts phenylsulfonylation of o-xylene, indan, and tetralin in nitrobenzene. Yoshii, Yoshihiro; Ito, Akiyoshi; Hirashima, Tsuneaki; Manabe, Osamu (Osaka Munic. Tech. Res. Inst., Osaka 536, Japan). Nippon Kagaku Kaishi, (8), 1117-21 (Japanese) 1986. CODEN: NKAKB8. ISSN: 0369-4577. DOCUMENT TYPE: Journal CA Section: 22 (Physical Organic Chemistry) Friedel-Crafts reactions of o-xylene, indan, and tetralin with PhSO2Cl in the presence of AlCl3 in PhNO2 were studied in relation to temp. effects on isomer distribution under kinetic conditions. In indan, the isomer ratio (3 to 4) increased with temp., while the ratio (3 to 4) decreased in o-xylene and in tetralin. Differences of activation energies and activation entropies in the 3- and 4-position for o-xylene, indan, and tetralin were -0.In this article, certain chemicals are used. One of their cas registry numbers is 108220-31-1 39 kcal/mol, -2.0 e.u./mol; 0.16, -0.2; and -0.31, -1.5. Isokinetic temp. were -81 and -62° for o-xylene and tetralin, resp. These results suggest that the 3-position of o-xylene or tetralin is more reactive than the 4-position, whereas the 4-position is more reactive in indan. The reaction proceeded with a concerted mechanism in which strong acid-catalytic effect by AlCl3 and base-catalyzed deprotonation by solvent and/or AlCl4- on the 3-position were obsd. in o-xylene and tetralin. .