Publication | Closed Access
Facile C–H Bond Metathesis Mediated by a Stannylene
45
Citations
46
References
2018
Year
The diarylstannylene, :Sn(Ar <sup>iPr4</sup>)<sub>2</sub> (Ar <sup>iPr4</sup> = C<sub>6</sub>H<sub>3</sub>-2,6-(C<sub>6</sub>H<sub>3</sub>-2,6- <sup>i</sup>Pr<sub>2</sub>)<sub>2</sub>), undergoes C-H metathesis with toluene, m-xylene, or mesitylene in solutions of these solvents at 80 °C. The products, [Ar <sup>iPr4</sup>Sn(CH<sub>2</sub>Ar)]<sub>2</sub> (Aryl=C<sub>6</sub>H<sub>5</sub> (1a), C<sub>6</sub>H<sub>4</sub>-3-Me (1b), C<sub>6</sub>H<sub>3</sub>-3,5-Me<sub>2</sub>(1c)) were characterized via <sup>1</sup>H, <sup>13</sup>C and <sup>119</sup>Sn NMR, UV-vis and IR spectroscopy, and by X-ray crystallography for 1a and 1b. A stoichiometric amount of the arene, Ar <sup>iPr4</sup>H, was also produced in these reactions. The use of EPR spectroscopy indicated the presence of a new type of one-coordinate, tin-centered radical, :ṠnAr <sup>iPr4</sup>, resulting from Sn-C bond cleavage in Sn(Ar <sup>iPr4</sup>)<sub>2</sub>.
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