Vinyl cation

For the functional group in general, see Vinyl group. For other uses, see Vinyl.

The vinyl cation is a carbocation with the positive charge on an alkene carbon. Its empirical formula of the parent ion is C
2H+
3. Vinyl cation are invoked as reactive intermediates in solvolysis of vinyl halides,[1][2] as well as electrophilic addition to alkynes and allenes.[3]

Note that unlike the allyl and benzyl carbocations (top left and right, respectively), the electron-deficient carbon of the vinyl carbocation (bottom) is double-bonded.
  1. ^ Okuyama, T. (2002). "Solvolysis of Vinyl Iodonium Salts. New Insights into Vinyl Cation Intermediates". Acc. Chem. Res. 35 (1): 12. doi:10.1021/ar0100374.
  2. ^ Gronheid, R (2001). "Thermal and Photochemical Solvolysis of (E)- and (Z)-2-Phenyl-1-Propenyl(phenyl)iodonium Tetrafluoroborate: Benzenium and Primary Vinylic Cation Intermediates". J. Am. Chem. Soc. 123 (36): 8760. doi:10.1021/ja010861n.
  3. ^ Walkinshaw, Andrew J.; Xu, Wenshu; Suero, Marcos G.; Gaunt, Matthew J. (2013). "Copper-Catalyzed Carboarylation of Alkynes via Vinyl Cations". Journal of the American Chemical Society. 135 (34): 12532–12535. doi:10.1021/ja405972h. PMID 23947578.