Synthesis, characterization, and reaction chemistry of [2-(2-pyridyl)ethyl]-, [2-(4-pyridyl)ethyl]-, and [2-(2-Oxo-N-pyrrolidinyl)ethyl]triphenyltin(IV)

Article abstract of DOI:10.1021/om00027a029

The compounds Ph₃SnR [R = (CH₂)₂C₅H₅N-2 (1), (CH₂)₂C₅H₅N-4 (2), and (CH₂)₂C₃H₆C(O)N-2 (3)] have been synthesized by hydrostannylation of 2- or 4-vinylpyridine and N-vinylpyrrolidin-2-one, respectively, with Ph₃SnH. Reaction of 1-3 with 1 equiv of X₂ (X = Br, I) gives Ph₂RSnX, which have been used to synthesize representative compounds of general formula Ph₂RSn(L), L = S₂CNR′₂ (R′ = Me, Et) or O₂CR′ (R′ = Me, Ph). The structures of the compounds are discussed on the basis of their ¹H, ¹³C, ¹¹⁹Sn NMR and ¹¹⁹Sn M?ssbauer data The structure of Ph₂Sn[(CH₂)₂C₅H ₅N-2](S₂CNMe₂) has been determined by X-ray crystallography: C₂₂H₂₄N₂S₂Sn, fw 499.28, a = 9.611 (4) ?, b = 10.255 (3) ?, c = 12.896 (9) ?, α = 75.35 (4)°, β = 70.97 (4)°, γ = 68.09 (3)°, V = 1102.2 ?³, Z = 2, space group P1, ρ_calc = 1.50 g cm^-3, μ(Mo Kα) = 12.42 cm^-1, λ(Mo Kα) = 0.710 69 ?, F(000) = 504, R = 0.0492, R_w = 0.0542 for 2133 unique data. The tin is in a five-coordinate, trigonal bipyramidal trans-NSSnPh₂R environment, with nitrogen and sulfur in the axial positions. The 2-ethylpyridyl ligand chelates the metal, while the dithiocarbamate is monodentate.