ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Anodic Oxidation of Organic Compounds, 23. - Anodic Addition of Ureas and Ethylene Glycol to Conjugated DienesThe anodic addition of 1,3-dimethylurea (4b) to 2,4-hexadiene (9), 2-methyl-2,4-hexadiene (10), 2,5-dimethyl-2,4-hexadiene (11), 1,3-cyclohexadiene (12), 1,4-diphenylbutadiene (13) and trans-stilbene (14) yields 4,5-disubstituted 1,3-dimethylimidazolidin-2-ones 16-23. Analogously 1,3-diphenylbutadiene (4c) adds to 9 to form 5-methyl-1,3-diphenyl-4-(1-propenyl)imidazolidin-2-one (24). Urea (4a) and 1,3-diacetylurea (4d) fail to react as a consequence of their insufficient nucleophilicity, N,N'-diacetylethylenediamine (4h) and 1,2-diacetylhydrazine (4g) do not undergo addition owing to their very low solubility in acetonitrile. In an electrolyte consisting of ethylene glycol/acetonitrile, 2,4-hexadiene (9) and 1,3-butadiene (8) afford the glycol ethers 25-28. The formation of all products can be explained in terms of a radical cation 29 as first intermediate.
Notes:
Die anodische Addition von 1,3-Dimethylharnstoff (4b) an 2,4-Hexadien (9), 2-Methyl-2,4-hexadien (10), 2,5-Dimethyl-2,4-hexadien (11), 1,3-Cyclohexadien (12), 1,4-Diphenylbutadien (13) und trans-Stilben (14) führt zu den 4,5-disubstituierten 1,3-Dimethylimidazolidin-2-onen 16-23. 1,3-Diphenylharnstoff (4c) addiert sich analog an 9 zu 5-Methyl-1,3-diphenyl-4-(1-propenyl)imidazolidin-2-on (24). Harnstoff (4a) und 1,3-Diacetylharnstoff (4d) lassen sich infolge zu geringer Nucleophilie, N,N'-Diacetylethylendiamin (4h) und 1,2-Diacetylhydrazin (4g) infolge zu geringer Löslichkeit in Acetoniril nicht anodisch mit 2,4-Hexadien (9) umsetzen. In einem Elektrolyten aus Ethylenglykol/Acetonitril entstehen aus 2,4-Hexadien (9) und 1,3-Butadien (8) die Glykolether 25-28. Alle Produkte lassen sich über ein primäres Radikalkation 29 erklären.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.197919790304
