Identification of Organic Compounds. IV. Chlorosulfonic Acid as a Reagent for Identification of Alkylbenzenes

Abstract

Vol. 63 of bromobenzene in 100 cc. of ether. Refluxing started immediately, and the solution was stirred for three hours. After standing overnight, decomposition was effected with ammonium chloride. A tertiary carbinol (15.4 g.) was obtained on evaporation of the ether which melted at 100-101°after recrystallization from methanol and petroleum ether.10 As described by Blicke,10 this carbinol gave a yellow color with sulfuric acid which disappeared on dilu-(1) This paper is constructed from part of a dissertation submitted in March, 1941, by John S. Autenrieth to the Faculty of the Massachusetts Institute of Technology in partial fulfillment of the requirements for the degree of Doctor of Philosophy.

Synthesis and Characterization of Oxotechnetium(V) Mixed-Ligand Complexes Containing a Tridentate N-Substituted Bis(2-mercaptoethyl)amine and a Monodentate Thiol

“…Ethylene sulfide, thiophenol, 2-methoxythiophenol, 3-methoxythiophenol, 4-methoxythiophenol, 4-toluenethiol, benzyl mercaptan, diethanolamine, (2-methoxyethyl)amine, N , N -dimethylethylenediamine, N , N -diethylethylenediamine, N , N -diethylpropylenediamine (Fluka Chemika), bromobenzene, iodobenzene, ethylbenzene, isopropylbenzene, butylbenzene, tert -butylbenzene, 1-naphthalenesulfonyl chloride, 4-methoxybenzyl chloride, 4- tert -butylbenzyl chloride, and 3,4-dimethylthiophenol, (Aldrich Chemical Co), where necessary were purified by distillation or by recrystallization. 4-Bromobenzenesulfonyl choride, 4-iodobenzenesulfonyl choride, 4-ethylbenzenesulfonyl choride, 4-isopropylbenzenesulfonyl choride, 4-butylbenzenesulfonyl choride, and 4- tert -butylbenzenesulfonyl choride were synthesized by a modification of a published procedure …”

Palladium‐Catalyzed ortho‐Benzoylation of Sulfonamides through C−H Activation: Expedient Synthesis of Cyclic N‐Sulfonyl Ketimines

“…5,7‐Dimethyl‐3‐phenyl‐benzo[ d ]isothiazole 1,1‐dioxide [28] ( 5 k ). Following the general procedure, the reaction of 2,4‐dimethy benzenesulfonamide with benzaldehyde gave 82 mg (61% yield) of 5 k as a white solid. M.P.…”

Intramolecular insertion of arylsulfonylnitrenes into aliphatic side chains

“…Found: C, 68.68; H, 10.12. Elution with ether gave mesitylene-2-sulfonamide (0.113 g, 30%), identical with an authentic sample. 19 Elution with ether-methanol (98:2 v/v) gave a tan solid which was sublimed (110 °C at 10 µ ) and recrystallized from light petroleum (bp 60-110 °C)-ethyl acetate to give colorless needles of 2,3-dihydro-5,7-dimethyl-1,2-benzoisothiazole 1,1-dioxide (0.118 g, 3.1%): mp 114. 5-115.5 °C; IR (KBr) 3220,1280,1170 cm"1; NMR (CDC13) 7.1 (s, 1, ArH), 7.01 (s, 1, ArH), 5.3-4.9 (br s, 1, exchanges with D20, NH), 4.46 (d, 2, Jc3h,nh = 5.6…”