Expanding the Scope of Sulfur-Centered Arbuzov Rearrangement in Diethyl/Di-n-propyl Sulfite for the Synthesis of Mixed-Ligand Di-n-butyltin Alkanesulfonates

Abstract

A one-pot reaction between di-n-butyltin oxide and diethyl/di-n-propyl sulfite in the presence of an equimolar amount of alkyl iodide proceeds via sulfur-centered Arbuzov rearrangement to afford the corresponding di-n-butyltin (alkoxy)alkanesulfonates n-Bu2Sn(OR')OS(O)2R [R = R' = Et (1), n-Pr (2); R = Me, R' = Et (3), n-Pr (4)]. The compounds 1 and 3 react with methylphosphonic acid under mild conditions to give [n-Bu2Sn(OS(O)2R)OP(O)(OH)Me]n [R = Et (5), Me (6), respectively].

Synthesis, characterization and structural studies of mixed-ligand di-n-butyltin alkanesulfonate derivatives, [n-Bu2Sn(X)OS(O)2R]2 [R=Et, n-Pr; X=acac, 4-OMe–O2CC9H5N-2, O2CC9H6N-2, O2CC9H6N-1]

“…In a recent communication, we have also reported the utility of diethyl/di-n-propylsulfite as a synthon to afford the corresponding di-n-butyltin(alkoxy)alkanesulfonates (Eq. (1)) [7].…”

The first structural characterization of a rare earth ethanesulfonate

“…In contrast, the anion containing atom S3 only acts as a monodentate ligand. Some -O:O 0 -bridging ethanesulfonate ligands are also found in dinuclear chloride-sulfonate-antimony(V) complexes (Burchardt et al, 1998;Lang et al, 1998) and in polymeric chains of the dioxouranium(VI) complex [(UO 2 )(H 2 O)(C 2 H 5 SO 3 ) 2 ] (Alcock et al, 1993) and the ethanesulfonate-hydrogenmethanephosphonate-diorganyltin(IV) compound [(C 4 H 9 ) 2 -Sn{OP(O)(OH)CH 3 }OS(O) 2 C 2 H 5 ] (Shankar et al, 2006). In contrast to this bridging mode, the ethanesulfonate group in the polymeric chain structure of [Cu(CO)C 2 H 5 SO 3 ] is 1O:2O 0 ,O 00 -bridging (Doyle et al, 1983).…”

Synthesis, Characterization, and Hydrolytic Behavior of Diorganotin(IV) Coordination Polymers with Layered Structural Motifs

“…We have reported a new family of layered mixed-ligand diorganotin (IV) 2 , which incorporate ring, ladder, and trinuclear tin cluster entities in their structural frameworks. [12] In a recent report, we demonstrated that the incorporation of silaalkylphosphonate ligands into diorganotin(IV) coordination polymers endows enhanced solubility in common organic solvents. This intrinsic property has been utilized to transform the bulk samples into colloidal dispersions featuring rod, rosette, and spherical morphologies.…”