Synthesis, crystal structures and coordination modes of some triorganotin(IV) complexes with 2-N-propyl and 2-N-benzyl-amino-1-cyclopentene-1-dithiocarboxylates

López-Cardoso, Marcela; Vargas-Pineda, Gabriela; Román-Bravo, Perla; Rodríguez-Narváez, Cristina; Rosas-Valdéz, Elena; Cea‐Olivares, Raymundo

doi:10.1016/j.molstruc.2016.03.010

Cited by 2 publications

(2 citation statements)

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“…Treatment of Mes 3 SbO with SnMe 3 Cl afforded similar results (Scheme A). The 119 Sn nucleus in the product resonates at −36.38 ppm in CDCl 3 , significantly upfield of Me 3 SnCl (169.1 ppm), and the 2 J SnH coupling (69.0 Hz) is stronger in the product. , These NMR data are consistent with the formation of a 5-coordinate Sn center in solution. Crystals of Mes 3 SbO → SnMe 3 Cl·(C 7 H 8 ) were grown from a concentrated toluene solution, and the solid-state structure was determined by SC-XRD.…”

Section: Resultssupporting

confidence: 63%

“…Mes 3 SbO → PbMe 3 Cl crystallized as the DCM solvate in space group P2 1 /c (Figure 3A). The Sb atom maintains a 63,64 These NMR data are consistent with the formation of a 5-coordinate Sn center in solution. Crystals of Mes 3 SbO → SnMe 3 Cl•(C 7 H 8 ) were grown from a concentrated toluene solution, and the solid-state structure was determined by SC-XRD.…”

Section: Journal Of the American Chemical Societysupporting

confidence: 71%

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A Sterically Accessible Monomeric Stibine Oxide Activates Organotetrel(IV) Halides, Including C–F and Si–F Bonds

Wenger,

Johnstone

2024

J. Am. Chem. Soc.

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Phosphine oxides and arsine oxides are common laboratory reagents with diverse applications that stem from the chemistry exhibited by these monomeric species. Stibine oxides are, in contrast, generally dimeric or oligomeric species because of the reactivity-quenching self-association of the highly polarized stiboryl (Sb=O/Sb + −O − ) group. We recently isolated Dipp 3 SbO (Dipp = 2,6-diisopropylphenyl), the first example of a kinetically stabilized monomeric stibine oxide, which exists as a bench-stable solid and bears an unperturbed stiboryl group. Herein, we report the isolation of Mes 3 SbO (Mes = mesityl), in which the less bulky substituents maintain the monomeric nature of the compound but unlock access to a wider range of reactivity at the unperturbed stiboryl group relative to Dipp 3 SbO. Mes 3 SbO was found to be a potent Lewis base in the formation of adducts with the main-group Lewis acids PbMe 3 Cl and SnMe 3 Cl. The accessible Lewis acidity at the Sb atom results in a change in the reactivity with GeMe 3 Cl, SiMe 3 Cl, and CPh 3 Cl. With these species, Mes 3 SbO formally adds the E−Cl (E = Ge, Si, C) bond across the unsaturated stiboryl group to form a 5-coordinate stiborane. The biphilicity of Mes 3 SbO is sufficiently potent to activate even the C−F and Si−F bonds of C(p-MeOPh) 3 F and SiEt 3 F, respectively. These results mark a significant contribution to an increasingly rich literature on the reactivity of polar, unsaturated main-group motifs. Furthermore, these results highlight the utility of a kinetic stabilization approach to access unusual bonding motifs with unquenched reactivity that can be leveraged for small-molecule activation.

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Section: Resultssupporting

confidence: 63%

Section: Journal Of the American Chemical Societysupporting

confidence: 71%