Room-temperature Transformation of Alkyl to Vinyl Carbocations in Organic Solutions: A New Path to Stable Vinyl Cation Salts
Evgenii S. Stoyanov *
N.N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia.
Irina V. Stoyanova
N.N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia.
*Author to whom correspondence should be addressed.
Abstract
It was found that alkyl carbocations, such as tert-butyl and methylcyclopentyl cations, decompose to unsaturated vinyl-type carbocations when their salts are dissolved in common organochlorine solvents. These transformations yield thermally stable vinyl cation salts, which were characterised by IR spectroscopy and, in some cases, X-ray crystallography. This method provides a convenient approach to isolating crystals of vinyl carbocation salts and studying them in solution, with implications for understanding carbocation stability and reactivity beyond superacidic media.
Keywords: Vinyl and alkyl carbocations, carborane salts, IR spectroscopy