Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany.
Beilstein J Org Chem. 2013 Dec 9;9:2834-40. doi: 10.3762/bjoc.9.318. eCollection 2013.
N-alkylation of N,N'-(hexane-1,6-diyl)bis(4-methylbenzenesulfonamide) with allyl bromide and subsequent Prilezhaev reaction with m-chloroperbenzoic acid to give N,N'-(hexane-1,6-diyl)bis(4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide) is described. This twofold alkylation was performed in aqueous solution, whereby α-, and randomly methylated β-cyclodextrin were used as adequate phase transfer catalysts and the cyclodextrin-guest complexes were characterized by (1)H NMR and 2D NMR ROESY spectroscopy. Finally, the curing properties of the diepoxide with lysine-based α-amino-ε-caprolactam were analyzed by rheological measurements.
N,N'-(己烷-1,6-二基)双(4-甲基苯磺酰胺)与烯丙基溴的 N-烷基化反应,以及随后与间氯过苯甲酸的普里莱泽夫反应,生成 N,N'-(己烷-1,6-二基)双(4-甲基-N-(环氧乙烷-2-基甲基)苯磺酰胺)。该双烷基化反应在水溶液中进行,其中 α-和随机甲基化的 β-环糊精用作合适的相转移催化剂,并且通过(1)H NMR 和二维 NMR ROESY 光谱对环糊精-客体配合物进行了表征。最后,通过流变学测量分析了二环氧与赖氨酸基 α-氨基-ε-己内酰胺的固化性能。