Willems, J. published the artcile< Aliphatic hydroxysulfonic acids and their internal esters: the sultones. II. The sultones>, Formula: C9H13NO3S, the main research area is .
CHR.(CH2)n.CHR’.SO2 (I) were prepared by concentration of an alc. solution of HOCHR(CH2)nCHR’SO3H (II) (from treating the Na salt in alc. with dry HCl) and distillation in vacuo (those of high mol. weight may decompose), by addition of Butyl Cellosolve (III) to the concentrated solution, distillation at 760 mm. until the b.p. (170°) of III is reached, and rectification in vacuo, and by addition of the alc. solution of II dropwise to boiling, stirred xylene (3 l. per mol), and the H2O distilled off as an azeotropic mixture of H2O-alc.-xylene until the b.p. of xylene is reached, the volume kept constant by dropwise addition of xylene, the solution cooled, washed with 2% NaHCO3 (important to keep from decomposition), and with H2O, dried, and the I obtained by distillation or precipitation with ligroine. The last method is generally applicable, simplest, and gives the best yields. The rate of reaction is not influenced by the pH, or by dehydrating agents. The reaction takes place near 150°, and not in low-boiling diluents, e.g. C6H6. 5- and 6-membered sultone rings are easily formed, and a 7-membered ring was obtained, but I could not be formed when n = 2 or 11. The following derivatives of I were prepared [R, n, R’, b.p./mm., m.p., d25, n25, M R, and m.p. of the corresponding pyridinoalkylsulfonic acid betaine (from boiling I in excess C5H5N), and its crystallizing solvent given]: H, 1, H (IV), 121°/1 (140°/8), 31°, -, -, -, 261°, alc.-H2O; H, 2, H (V), 153°/14, 15°, 1.3319, 1.4615, 28.15, 239°, isoamyl alc.; Me, 1, H (VI), 124°/2 (157.5°/14), -, 1.2929, 1.4500, 28.20, 240°, EtOH; H, 1, Me (VII), 124°/1.5, -, 1.3004, 1.4525, 28.24, 246°, MeOH; Me, 1, Me, 129°/1, -, 1.2220, 1.4511, 33.00, 270-71°, EtOH; H, 3, H (VIII), 155-6°/2, -, 1.2542, 1.4605, 32.65, 233-4°, EtOH; Me, 1, Pr (IX), 143-3.5°/4.2, -, 1.3359, 1.4520, 42.10, 230-32°, BuOH-Et2O; Bu, 1, H, 141°/2, -, -, -, -, 262-3°, EtOH-Et2O; Pr, 2, H, 126°/0.4, -, -, -, -, 263-4°, EtOH-Et2O; Me2CH(CH2)2, 1, H, 130°/1.5, -, -, -, -, 229-30°, absolute EtOH-Et2O; Me, 1, Me(CH2)5, 145°/0.6, -, -, -, -, 185°, EtOH-Et2O; Me(CH2)7, 1, H, 160-3°/0.5, -, -, -, -, 222.5-3.0°, BuOH; Me, 1, Me(CH2)13, -, half solid oil, -, -, -, 155°, EtOH/Et2O; Me(CH2)15, 1, H, -, 81° (EtOH), -, -, -, 214-15°, absolute EtOH; Me, 1, Ph, -, 106° (EtOH), -, -, -, 295-6.5°, EtOH-H2O. Also prepared were: O.CHMe.CH2.CMe2.SO2 (X), 160°/16, 50.5° (ligroine-Et2O), -, -, -, 253-4°, AmOH; O.CHMe.CHMe.CHPr.SO2, 128°/1.5, -, -, -, -, 245-6°, BuOH; O.CHMe.CHMe.CH[(CH2)5Me].SO2, 155°/1.5, -, -, -, -, -, – (C5H5N derivative very hygroscopic). Anilino sulfonic acids (PhNHCHRCH2CHR’SO3H) were prepared quant. by boiling equivalent amounts of PhNH2 and the following sultones 3-4 h. in C6H6 (m.p. of the PhNH derivative and crystallizing solvent given): IV, 248-9°, 90% EtOH; VI, 276-8°, H2O; VII, 254°, MeOH; X, 267-8°, EtOH; IX, 235.5-6°, BuOH. The reactions with PhNH2 and C5H5N show I to be alkylating agents, which provide a method for introducing the SO3 group and the attendant H2O solubility into certain compounds Also 1.g. IV mixed in a mortar with 1.09 g. p-H2NC6H4OH, the mixture heated 30 min. on the H2O bath, boiled with Me2CO to remove unreacted p-H2NC6H4OH, and crystallized from H2O, yielded 83% p-HOC6H4NH(CH2)3SO3H, m. 249°; 1.36 g. V boiled 6 h. in 25 cc. xylene with 1.29 g. octylamine gave Me(CH2)7NH(CH2)4SO3H.H2O, m. 172-3°. V (2.72 g.) with 2.88 g. β-naphthol in 0.8 g. NaOH solution precipitated immediately β-C10H7O(CH2)4CO3Na (beautiful crystals from EtOH-H2O). Similarly, VIII yielded 93% β-C10H7O(CH2)5SO3Na. The sultones keep their sulfoalkylating properties when reacting with RMgBr. V (13.6 g.) in absolute Et2O, dropped into Et2O containing EtMgBr (from 10.9 g. EtBr and 3 g. Mg) yielded 60% Me(CH2)5SO3K (phenylhydrazine salt, m. 101.5-2°, gave no depression of the m.p. of an authentic sample).
Bulletin des Societes Chimiques Belges published new progress about Lactones, sultones. 21876-43-7 belongs to class pyridine-derivatives, and the molecular formula is C9H13NO3S, Formula: C9H13NO3S.