Oxidation of Cucurbituril and Its Analogues

Lü, Hong‐Yan; Shi, Daxin; Zhang, Qi; Yang, Dixiong; Li, Jiarong

doi:10.6023/cjoc201409002

Cited by 1 publication

(2 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Oxidation of CB[6] could produce oxalic acid [ 23 ], and we found urea during the hydrolysis of glycoluril. These were both solid proof that these compounds were able to be hydrolysed to give glyoxal.…”

Section: Resultsmentioning

confidence: 99%

“…In 2003, Kim and co-workers [ 22 ] first reported the reaction of CB[6] with K 2 S 2 O 8 producing perhydroxycucurbit[6]uril. Based on Kim's research, Li and co-workers further investigated the type of oxidant and optimized the reaction conditions, but it was still very difficult to control the depth of oxidation [ 23 ]. The synthesis of monofunctionalized CB[ n ] in a controlled environment also has several successful examples.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Investigation on the hydrolytic mechanism of cucurbit[6]uril in alkaline solution

et al. 2018

Self Cite

View full text Add to dashboard Cite

The structure of cucurbit[6]uril (CB[6]), as a fascinating supramolecular receptor, is regarded as ‘indestructible’. Herein, we investigated the hydrolysis of CB[6] catalysed by alkali. Our results showed that CB[6] was easily hydrolysed in 30% NaOH at 160°C within 3 h. Separation and purification of hydrolytic products demonstrated the presence of NH3, CO2, HCOONa, glycine and hydantoic acid. Based on the studies of the hydrolysis of substances similar to CB[6] including 4,5-dihydroxyethyleneurea, glycoluril and glycoluril dimer, we proposed that a plausible reaction mechanism involved a Cannizzaro reaction, which is supported by HPLC, mass spectrometry data and previous reports. Further studies are dedicated towards a controlled hydrolysis of CB[6], which will provide a new route for direct functionalization of CB[6].

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%