Abstract
The reaction of 2-ethyl-3-tetrahydrofuryl thiocyanate (I) and triphenylacetonitrile (VIII) with methylmagnesium iodide in ether was studied using GC/MS, PMR and13C NMR spectroscopy. The reaction of (I) with CH3MgI gives the product of the homolysis of the C-S σ bond, namely, bis(2-ethyl-3-tetrahydrofuryl) disulfide (II), in 81% yield. This reaction is assumed to be general in nature since triphenylacetonitrile (VIII) is also homolytically cleaved by the action of CH3MgI to give triphenylmethane.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2886–2888, December, 1991.
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Polivin, Y.N., Karakhanov, R.A., Sheveleva, T.S. et al. Homolytic dissociation of the carbon-element σ bonds by Grignard reagents. Russ Chem Bull 40, 2518–2520 (1991). https://doi.org/10.1007/BF00959737
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DOI: https://doi.org/10.1007/BF00959737