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Quantification of the Electrophilicities of Dithiocarbenium Ions

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image of Research on Chemical Intermediates

The reactions of the dithio substituted carbenium ions 2a-c with allylsilanes, allylstannanes (3), and silylated enol ethers (4) which yield dithioacetal protected β,γ-unsaturated carbonyl compounds (7) and selectively protected 1,3-dicarbonyl compounds (8), have been studied kinetically. The second-order rate constants have been used to determine the electrophilicity parameters for the [1,3]dithiolan-2-ylium ion 2a (E = -6.25) and the [1,3]dithian-2-ylium ions 2b (E = -6.82) and 2c (E = -2.17). It is shown how these parameters can be used to predict the electrophilic potential of 2a-c.

Affiliations: 1: Institut für Organische Chemie der Technischen Hochschule Darmstadt, Petersenstraße 22, D-64287 Darmstadt, Germany


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