80262-44-8Relevant articles and documents
Synthesis of Disubstituted Cucurbit[6]uril and Its Rotaxane Derivative
Isobe, Hiroyuki,Sato, Sota,Nakamura, Eiichi
, p. 1287 - 1289 (2002)
(Matrix Presented) Synthesis of diphenyl cucurbit[6]uril (CB[6]) has been achieved via co-oligomerization of diphenyl glycoluril and unsubstituted glycoluril. The unsymmetrically substituted CB[6], Ph2CB[B], was further converted to a rotaxane incorporating bis(dinitrophenyl)spermine.
PROCESS FOR THE PREPARATION OF CUCURBITURIL DERIVATIVES
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Page/Page column 14; 15, (2018/07/22)
This invention relates to cucurbituril and/or one or more derivatives thereof with low formaldehyde content, to a process of manufacturing said cucurbituril and/or one or more derivatives thereof and to the use of said cucurbituril and/or one or more derivatives thereof, in particular in consumer and industrial products, and in industrial processes.
Cucurbit[n]uril formation proceeds by step-growth cyclo-oligomerization
Huang, Wei-Hao,Zavalij, Peter Y.,Isaacs, Lyle
supporting information; scheme or table, p. 8446 - 8454 (2009/02/02)
In contrast to the high yield formation of cucurbit[n]uril (CB[n]) from a 1:2 ratio of glycoluril to formaldehyde, the condensation of glycoluril with less than 2 equiv of formaldehyde delivers a reaction mixture that contains glycoluril oligomers (2-6) and CB[n] compounds that lack one or more methylene bridges known as nor-seco-cucurbit[n]urils (ns-CB[n]). In this paper we report the chromatographic purification of C-shaped glycoluril oligomers (dimer-hexamer), their characterization in solution, and their X-ray crystal structures. Quite interestingly, despite being acyclic glycoluril pentamer 5 and hexamer 6 retain the ability to bind to guests typical of CB[6] but are also able to expand their cavity to accommodate larger guests like cationic adamantane derivatives. We performed product resubmission experiments with glycoluril oligomers 2-6 and found preferences for the formation of specific ring sizes during CB[n] formation. A comprehensive mechanistic scheme is proposed that accounts for the observed formation of 2-6 and ns-CB[n]. Overall, the experiments establish that a step-growth cyclo-oligomerization process operates during CB[n] formation.