Syntheses, structures, and¹H,¹³C{¹H} and¹¹⁹Sn{¹H} NMR chemical shifts of a family of trimethyltin alkoxide, amide, halide and cyclopentadienyl compounds

Abstract

The synthesis and full characterization, including Nuclear Magnetic Resonance (NMR) data ((1)H, (13)C{(1)H} and (119)Sn{(1)H}), for a series of Me3SnX (X = O-2,6-(t)Bu2C6H3 (), (Me3Sn)N(2,6-(i)Pr2C6H3) (), NH-2,4,6-(t)Bu3C6H2 (), N(SiMe3)2 (), NEt2, C5Me5 (), Cl, Br, I, and SnMe3) compounds in benzene-d6, toluene-d8, dichloromethane-d2, chloroform-d1, acetonitrile-d3, and tetrahydrofuran-d8 are reported. The X-ray crystal structures of Me3Sn(O-2,6-(t)Bu2C6H3) (), Me3Sn(O-2,6-(i)Pr2C6H3) (), and (Me3Sn)(NH-2,4,6-(t)Bu3C6H2) () are also presented. These compiled data complement existing literature data and ease the characterization of these compounds by routine NMR experiments.

Synthesis of Aminobismuthanes via Me3SnCl Elimination

“…The crystal structure of 3 was recently published by Nelson and Kiplinger . Although 3 was crystallized form benzene at room temperature (this work) and not from acetonitrile at –30 °C ( Nelson and Kiplinger ), the same modification was obtained in good agreement with our data set.…”

Preparation of single-site tin(IV) compounds and their use in the polymerization of ε-caprolactone

“…Organotin(IV) derivatives show variety of applications ranging in all sorts of biological activities as anticancer, antiviral, antibacterial and antifungal agents, wood preservatives, pesticides, etc., precursors for hybrid inorganic–organic nano and non-linear optical materials, catalysts for organic carbon–carbon coupling and ring opening processes. [ 1–5 ] Despite their broad utilities, it is surprising that there is very little information about the synthesis of single-site organotin derivatives and their usage as catalysts in the ring opening of cyclic esters such as ε-caprolactone or L-lactide. [ 6,7 ] The single-site catalyst has a general formula of L n RMX (M: Metal, R: alkyl or aryl).…”

Synthesis of Actinide Fluoride Complexes Using Trimethyltin Fluoride as a Mild and Selective Fluorinating Reagent

“…If desired, the Me 3 SnX (X = Cl, Br, I) can be subsequently converted back into Me 3 SnF by reaction with aqueous KF solution , , . When the reactions are monitored by 1 H NMR spectroscopy in [D 6 ]benzene, resonances corresponding to the uranium(V) imido halide complex ( 4 ), in addition to singlets at δ = 0.29, 0.40, and 0.48, are observed for Me 3 SnX (X = Cl, Br, and I), respectively, consistent with a halide exchange reaction . Previously, complex 4 was synthesized by the oxidation of (C 5 Me 5 ) 2 U(=N‐2,6‐ i Pr 2 C 6 H 3 )(THF) with excess CuF 2 ,[9b] whereas the current procedure is redox‐neutral.…”

“…One interesting observation made during the course of these studies was that the liberated Me 3 SnCl and Me 3 SnI in reactions 2–4 can react with the uranium aryloxide and amide ancillary linkages in (C 5 Me 5 ) 2 U(F)(O‐2,6‐ i Pr 2 C 6 H 3 ) ( 6 ), U(F)(O‐2,6‐ t Bu 2 C 6 H 3 ) 3 ( 8 ) and U(F)[N(SiMe 3 ) 2 ] 3 ( 10 ) to form the corresponding trimethyltin derivatives Me 3 Sn(O‐2,6‐ i Pr 2 C 6 H 3 ) [ δ [D6]benzene = 0.25 (SnC H 3 ), 1.27 ( i Pr‐C H 3 ), 3.38 ( i Pr‐C H ), 6.93 ( p ‐Ar– H ), 7.12 ( m ‐Ar– H )], Me 3 Sn(O‐2,6‐ t Bu 2 C 6 H 3 ) [ δ [D6]benzene = 0.32 (SnC H 3 ), 1.49 ( t Bu‐C H 3 ), 6.90 ( p ‐Ar– H ), 7.35 ( m ‐Ar– H )], and Me 3 SnN(SiMe 3 ) 2 [ δ [D6]benzene = 0.21 (SiC H 3 ), 0.25 (SnC H 3 )], respectively, which were identified by monitoring the reactions by 1 H NMR spectroscopy . We found that this side reaction is circumvented by immediately placing the reactions under reduced pressure after the Me 3 SnF is added such that volatile Me 3 SnX (X = Cl, Br, I) compounds are removed as they are formed.…”