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Generation and Characterization of 1,2-diaryl-1,1,2,2-tetramethyldisilane Cation Radicals

Generation and Characterization of 1,2-diaryl-1,1,2,2-tetramethyldisilane Cation Radicals

Gonzalo Guirado, Olesya Haze, Joseph P Dinnocenzo

J Org Chem. 2010 May 21;75(10):3326-31.

PMID: 20405871

Abstract:

Nanosecond laser flash photolysis methods were used to generate and spectrally characterize the cation radicals of 1,2-diaryl-1,1,2,2,-tetramethyldisilanes (Ar = p-X-Ph, X = H, CH(3), OCH(3)) in hexafluoroisopropanol (HFIP) at room temperature. The disilane cation radicals rapidly reacted with methanol, with bimolecular rate constants ranging from 0.63 to 2.1 x 10(8) M(-1) s(-1). The cation radicals were found to react with tert-butanol 4-5 times more slowly than methanol, consistent with a small steric effect for nucleophile-assisted fragmentation of the Si-Si bond. The standard potentials for oxidation of the disilanes in HFIP were determined by two different methods: first, by measuring equilibrium constants for electron exchange between the disilanes and the cation radical of hexaethylbenzene and, second, by combining electrochemical data from cyclic voltammetry with the lifetimes of the disilane cation radicals measured by laser flash photolysis in the same media. Agreement between the two methods was excellent (

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP814982	1,1,2,2-Tetramethyldisilane		814-98-2	Price

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