【摘要】 一种可循环使用的固相试剂:N-烷基-N-酰基磺酰胺聚苯乙烯基微球(5),通过对聚苯乙烯磺酰氯微球树脂进行两步功能基化的修饰反应来制备.制备过程如下:聚苯磺酰氯树脂(1)与伯胺(2)反应得到聚苯乙烯基N-烷基磺酰胺树脂(3),树脂3用酰氯(4)或酸酐酰化得到N-烷基-N-酰基磺酰胺聚苯乙烯基树脂(5).酰化的树脂5作为酰基转移试剂与亲核试剂胺反应得到二级酰胺.根据5上取代基对酰胺生成的程度的影响结果表明,烷基R1和酰基(R2CO)对酰基转移反应活性的大小依次分别为:苯基>苄基>甲基>正丁基>>H和对硝基苯甲酰基>苯甲酰基>乙酰基.胺的亲核能力对酰胺的收率也有一定的影响.N-苯基-N-苯甲酰基磺酰胺树脂重复使用3次没有发现活性降低.更多还原

【Abstract】 Polystyrene supported N-alkyl-N-acyl sulfonamide resins (5) were prepared through a two-step modification reaction on polymer beads and developed as an effective type of recyclable solid-phase re- agents. Polystyrene sulfonyl chloride (1) reacted with primary amines (2) to afford supported N-alkyl sul- fonamide resins (3), and the resin 3 was acylated using either acyl chloride 4 or acidic anhydride in pyridine to afford the resins 5. Reaction of the acylated sulfonamide resins 5 as acyl transfer reagents with nucleo- philic amines yielded the secondary amides. It was found that the substituents of N-alkyl(R1)-N-acyl(R2CO) sulfonamide resins had significant influences on the acyl transfer reaction. According to the acyl transfer reactivity of N-alkyl-N-acyl sulfonamide resins (5), alkyl group R1 was ordered as follows: phenyl>benzyl >methyl>n-butyl>>H, and R2CO: p-nitrobenzoyl>benzoyl>acetyl. The nucleophilic ability of the amines had effect on the yields of the amides as well. The N-phenyl-N-benzoyl sulfonamide resin (5hb) was found to be regenerated three times without loss of their activity.更多还原