Preparation of (mono)sulfonates: Suitable precursors for unnatural sulfonolipids

Article type: Research Article

Authors: Ioannou, Panayiotis V.^{; *} | Tsivgoulis, Gerasimos M.^{; *}

Affiliations: Department of Chemistry, University of Patras, Patras, Greece

Correspondence: [*] Corresponding author: P.V. Ioannou, Department of Chemistry, University of Patras, 26504 Patras, Greece. Fax: +30 2610 997118; E-mails: ioannou@chemistry.upatras.gr (P.V. Ioannou), tsivgoulis@chemistry.upatras.gr (G. M. Tsivgoulis)

Abstract: Aiming at the preparation of the novel unnatural, non-isosteric sulfonolipids bearing one, two and three acyl groups 8, 9 and 10, their precursors hydroxyl-containing sulfonates have been prepared from a variety of hydroxyl-containing halogenides and epoxides using the Strecker reaction. Thus, the sulfonates 16 and 22 were prepared pure, while the sulfonate 27 could only be prepared as a by-product using 1,4-dibromo-2,3-butanediol 26 and in low yields. For these reactions, probable pathways leading to the isolated or spectroscopically identified products are proposed. Conclusions about the relative nucleophilicity of SO32- compared to AsO33 - (as well as HO- which is present in their aqueous solutions) were drawn based on the yields of the corresponding arsonic acids and sodium sulfonates. The IR (KBr) and 1H NMR (D2O) spectra of sulfonates (and in some cases of their sulfonic acids) are analyzed and discussed.

Keywords: The Strecker reaction, hydroxy (mono)sulfonates

DOI: 10.3233/MGC-210014

Journal: Main Group Chemistry, vol. 20, no. 2, pp. 103-118, 2021