- N-Ethyldiisopropylamine and Sulfur Dioxide Solutions. 2. Reactions with Conjugate Acceptors
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Solutions of sulfur dioxide and N-ethyldiisopropylamine (EDIA) are able to reduce α,β-unsaturated-γ-dicarbonyl compounds (esters or ketones) into α-dicarbonyl alkanes.In contrast, monoactivated Michael acceptors, such as acrylates, give symmetrical sulfones.These processes involve the conjugate addition of HSO2(-), formed from a charge-transfer complex between EDIA and SO2.Secondary amines are formed as byproducts.Triethylamine, which forms a more stable complex with sulfur dioxide than EDIA, is far less reactive toward the same substrates.
- Eugene, Fabrice,Langlois, Bernard,Laurent, Eliane
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p. 2599 - 2603
(2007/10/02)
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