Thio- and selenocarbonyl compounds as "Superdienophiles" in [4+2] cycloadditions

Rohr, Uwe and Schatz, Jürgen and Sauer, Juergen (1998) Thio- and selenocarbonyl compounds as "Superdienophiles" in [4+2] cycloadditions. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (12). pp. 2875-2883. ISSN 1434-193X, 1099-0690

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Abstract

Normal, neutral, and inverse-type Diels-Alder reactions can be observed in [4+2] cycloadditions of thio- and selenocarbonyl compounds 1-9 with various cyclic and aryl-, methyl- or methoxy-substituted open-chain 1,3-butadienes. Extensive kinetic studies prove the highly dienophilic activity of the C=S and C=Se double bond. Studies of the solvent and temperature dependence of the reaction rate indicate a concerted mechanism.

Item Type: Article
Uncontrolled Keywords: DIELS-ALDER-REACTIONS; REACTIVITY; SUPERDIPOLAROPHILES; REGIOSELECTIVITY; THIOBENZOPHENONE; SCALE; WATER; cycloadditions; substitution effects; thiocarbonyl compounds; selenocarbonyl compounds; solvent effects
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 21 Feb 2023 07:17
Last Modified: 21 Feb 2023 07:17
URI: https://pred.uni-regensburg.de/id/eprint/49287

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