N-Ethyldiisopropylamine and Sulfur Dioxide Solutions. 2. Reactions with Conjugate Acceptors

F Eugene, B Langlois, E Laurent

Index: Eugene, Fabrice; Langlois, Bernard; Laurent, Eliane Journal of Organic Chemistry, 1994 , vol. 59, # 9 p. 2599 - 2603

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Citation Number: 8

Abstract

Solutions of sulfur dioxide and N-ethyldiisopropylamine (EDIA) are able to reduce a, j3- unsaturatedy-dicarbonyl compounds (esters or ketones) into a-dicarbonyl alkanes. In contrast, monoactivated Michael acceptors, such as acrylates, give symmetrical sulfones. These processes involve the conjugate addition of HS02-, formed from a charge-transfer complex between EDIA and S02. Secondary amines are formed as byproducts. ...