Herbrandson, Harry F. published the artcileDerivatives of aromatic sulfinic acids. II. The reaction of thionyl chloride with sulfinic esters, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Journal of the American Chemical Society (1956), 2576-8, database is CAplus.
cf. C.A. 49, 9370i. PhSOCl (22.5 g.) added to 11.1 g. dry pyridine and 5 g. absolute MeOH in 60 cc. dry Et2O, the mixture kept at -10° until no more precipitate was formed, and diluted with H2O, the Et2O layer washed, dried, and evaporated, and the residue distilled yielded 14.0 g. PhSO2Me (I), b0.04 67-8°, b0.03 63°, nD20 1.5400. In the same manner was prepared p-MeC6H4SO2Me (II), 91%, b0.001 68°, nD20 1.5380. II (20.1 g.) and 14.0 g. pure SOCl2 kept a few days in the dark and distilled gave 3.5 g. ClCO2Me, b. 104-6°, nD20 1.4629, and 18.7 g. p-MeC6H4SOCl, lemon-yellow oil, b0.012 79°, nD20 1.6007; it gave with NH3 in dry Et2O the p-MeC6H4SONH2, m. 120-20.5° (from aqueous EtOH). I gave in the same manner 84% PhSOCl, yellow oil, b0.012 65° [PhSONH2, m. 122° (from aqueous EtOH); piperidide, m. 82-3° (from petr. ether)]. l-Menthyl 1-p-toluenesulfinate (III), m. 106-7° (corrected), [α]D25 -199.19° (c 2, Me2CO), was prepared by the method of Phillips (C.A. 20, 397). Et4NBr in H2O treated with a slight excess Ag2O, the mixture triturated twice, and the filtrate acidified to Congo red with 20% HCl and evaporated gave Et4NCl (IV). A series of kinetic runs was carried out with III and SOCl2 in PhNO2 at 24.88 ± 0.05° (molar concentrations of IV, SOCl2, and IV, and k × 104 sec.-1 given): 0.0554, 0.0616, 0.00093, 0.62; 0.0551, 0.0616, 0.00-213, 1.18; 0.0626, 0.0616, 0.00309, 1.68; 0.0590, 0.123, 0.00309, 1.92; 0.0516, 0.0616, 0.00425, 2.30; 0.0604, 0.0616, 0.00463, 2.06; 0.0779, 0.0616, 0.00463, 2.12; 0.0520, 0.0616, 0.00850, 3.55; 0.0409, 0.0616, 0.0106, 3.80; 0.0635, 0.0616, 0.0160, 4.28; 0.0548, 0.0492, 0.0213, 3.82; 0.0423, 0.0492, 0.0213, 4.24; 0.0774, 0.123, 0, 0; 0.0542, 0, 0.00617, 0; 0.0845, 0, 0.0213,0; 0.0663, 0, – (0.00525 HCl), 0; 0.0594, 0.0616, – (0.00525 HCl), 0; 0.0510, 0.0616, 0.00378 (MeOH), 0; 0.0408, 0.0616, – (0.0035 H2O), 0; 0.0732, 0.0860, 0.0232, 7.30; 0.0703, 0.0860, 0.0232 + 0.1M SO2, 7.63. In the absence of added chloride the reaction is slow; it is 1st order in ester and 1st order in added chloride ion. Trace impurities of the SOCl2, probably mainly HCl, also affect the rate.
Journal of the American Chemical Society published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Safety of 1-(Phenylsulfinyl)piperidine.
Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem