Day A, Arnold A P, Blanch R J, Snushall B
School of Chemistry, University College, University of New South Wales, Australian Defence Force Academy, Canberra, ACT 2600, Australia.
J Org Chem. 2001 Nov 30;66(24):8094-100. doi: 10.1021/jo015897c.
The acid-catalyzed synthesis of cucurbit[n]urils from formaldehyde and glycoluril is poorly understood. In this paper, we examine a wide range of reaction conditions that include the effects of acid type, acid concentration, reactant concentrations, and temperature to both probe the mechanism and optimize the yields of isolated cucurbit[n]urils, where n = 5-10. A mechanism for the formation of these cucurbit[n]urils is presented. Individual cucurbit[n]urils were unambiguously identified in reaction mixtures using ESMS and (13)C NMR.
由甲醛和甘脲通过酸催化合成葫芦[n]脲的反应机理目前还不太清楚。在本文中，我们研究了广泛的反应条件，包括酸的类型、酸浓度、反应物浓度和温度的影响，以此来探究反应机理并优化分离得到的葫芦[n]脲（n = 5 - 10）的产率。文中还提出了这些葫芦[n]脲的形成机制。利用电喷雾质谱（ESMS）和碳-13核磁共振（(13)C NMR）对反应混合物中的各个葫芦[n]脲进行了明确鉴定。
