N-Ethyldiisopropylamine and Sulfur Dioxide Solutions. 2. Reactions with Conjugate Acceptors
作者:Fabrice Eugene、Bernard Langlois、Eliane Laurent
DOI:10.1021/jo00088a051
日期:1994.5
Solutions of sulfur dioxide and N-ethyldiisopropylamine (EDIA) are able to reduce alpha,beta-unsaturated-gamma-dicarbonyl compounds (esters or ketones) into alpha-dicarbonyl alkanes. In contrast, monoactivated Michael accepters, 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.