Condensation of Diacetyl with Alkyl Amines: Synthesis and Reactivity of p-Iminobenzoquinones and p-Diiminobenzoquinones

Autor: Rafael Bautista, Vanessa Pelayo, Saúl Frias-Puente, Joaquín Tamariz, Carlos Espinoza-Hicks, Francisco Delgado, Eder I. Martínez-Mora
Jazyk: angličtina
Rok vydání: 2015
Předmět:
Zdroj: Molecules, Vol 20, Iss 11, Pp 20719-20740 (2015)
Molecules
Volume 20
Issue 11
Pages 20719-20740
Molecules; Volume 20; Issue 11; Pages: 20719-20740
ISSN: 1420-3049
Popis: Condensation reactions between diacetyl and α-branched primary alkylamines under mild and neutral conditions provided a mixture of 2,5-dimethylbenzoquinone(alkylimines), 2,5-dimethylbenzoquinone(bis-alkyldiimines), and N,N′-dialkyl-2,5-dimethylbenzene-1,4-diamines, which were efficiently separated as pure products by column chromatography. Both 2,5-dimethylbenzoquinone(alkylimines) and 2,5-dimethylbenzoquinone(bis-alkyldiimines) underwent an interchange of the alkylimino group when treated with anilines, followed by reductive aromatization, to provide diarylamines and 1,4-dianilinobenzenes, respectively. Evaluation was also made of the reactivity and selectivity of these compounds in the presence of anilines, thiophenols and alkylhalides.
Databáze: OpenAIRE
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