Preparation of p-nitrocalix[n]arene methyl ethers via ipso-nitration and crystal structure of tetramethoxytetra-p-nitrocalix[4]arene

Kumar, Satish; Varadarajan, R.; Chawla, Har Mohindra; Hundal, Geeta; Hundal, Maninder Singh

doi:10.1016/j.tet.2003.11.057

Cited by 22 publications

(12 citation statements)

References 12 publications

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“…Subsequently, nucleophilic attack of the resulting 4a to H 3 PO 4 under high temperature, followed by loss of isobutene, led to the formation of 5. The mechanism is analogous to the de-tert-butylation of ptert-butylcalix[n]arene in literature [21].…”

mentioning

confidence: 69%

Facile synthesis of 10‐tert‐butyl[1]benzoxepino[3,4‐b][1,3] dioxolo[4,5‐g]quinolin‐12(6H)‐ones

Zhang

Sun

et al. 2009

Journal of Heterocyclic Chem

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mentioning

confidence: 69%

Facile synthesis of 10‐tert‐butyl[1]benzoxepino[3,4‐b][1,3] dioxolo[4,5‐g]quinolin‐12(6H)‐ones

Zhang

Sun

et al. 2009

Journal of Heterocyclic Chem

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“…The standard redox potentials, E o , of NO [28]. Coincidentally, nitration of a calixarene compound by anhydrous AlCl 3 and KNO 3 in CH 2 Cl 2 has been reported [29]. Another aluminum salt, Al(H 2 PO 4 ) 3 , serves as an efficient solid acid catalyst of nitration of a variety of organic substances with 70 % nitric acid [30].…”

Section: Evolution Of CL 2 In Concentrated Chloride Salt Solutions Anmentioning

confidence: 99%

Mechanism of enhanced oxidation ability of dilute nitric acid and dissolution of pure gold in seawater with nitric acid

Hojo

2019

Chemical Series

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It has been discovered that dilute nitric acid in reversed micelle systems can oxidize the Br ion to Br 2 and we have proposed that the nitryl (or nitronium) ion NO 2 + should be the active species in the oxidation process. Nitration of phenol in reversed micelle systems with dilute nitric acid, CHCl 3 /CTAC/H 2 O (2.0 mol dm-3 HNO 3 in the 1.0% (v/v) H 2 O phase), has been performed at 35 ºC to obtain 2-and 4-nitrophenols, where CTAC represents cetyltrimethylammonium chloride. In aqueous 2.0 mol dm-3 HNO 3 solution accompanied by 4.0 mol dm-3 LiCl (and a small amount of LiBr as the bromide resource), trans-1,4-dibromo-2-butene was successfully brominated to 1,2,3,4-tetrabromobutane. This result is good evidence that the Br ion can be oxidized to Br 2 in dilute nitric acid (2.0 mol dm-3) providing it contains concentrated salts. For chloride salts, the cation effects increased as Et 4 N + << Na + < Li + < Ca 2+ < Mg 2+. Even the evolution of Cl 2 has been demonstrated from < 2.0 mol dm-3 HNO 3 solution containing concentrated LiCl, MgCl 2 , and CaCl 2 as well as AlCl 3. The dissolution of precious metals (Au, Pt, and Pd), especially, of gold has been demonstrated in 0.1-2 mol dm-3 HNO 3 accompanied by alkali metal, alkaline earth metal, and aluminum chlorides. The complete dissolution time of pure gold plate (20±2 mg, 0.1 mm thickness) in 2.0 mol dm-3 HNO 3 accompanied by 1.0 mol dm-3 AlCl 3 has been shortened remarkably with temperature increase from 15 to 80 ºC. The dissolution rate constants, log (k /s-1), of a piece of gold wire (19.7±0.5 mg) in 20 mL of 2.0 mol dm-3 HNO 3 accompanied by the metal chlorides, in general, increase with increasing salt concentrations at 40 and 60 ºC. The gold can be dissolved in the solution of <1.0 mol dm-3 HNO 3 and <1.0 mol dm-3 HCl, i.e. a "dilute aqua regia." We have achieved a total dissolution of five pieces of the gold wire (totally 0.10 g) in 100 mL of the 1:1 mixture between seawater and 2.0 mol dm-3 HNO 3 at ca. 100 ºC.

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“…The calixarenes with all etherified phenol rings could be successfully nitrated, but calixarenes with free hydroxyl groups at lower rim failed to produce nitrocalixarenes due to serious side reactions such as oxidation by the fuming nitric acid [9,10]. Later, it was found that some other nitration reagents such as AlCl 3 /KNO 3 , HNO 3 /CH 3 COOH, HNO 3 /(CH 3 CO) 2 O, Ce(IV)NH 4 (NO 3 ) 5 /CH 3 COOH), [11][12][13][14][15][16] and even NO 2 gas [17], could successfully realize the nitration, not only for etherified calixarenes but also for calixarenes with free hydroxyl groups at lower rim under mild reaction condition. Among these nitration reagents, the mixture of 65 % HNO 3 and CH 3 COOH is the most popular one because it often brings to high yield and simple work-up for the nitration of calixarenes.…”

Section: Introductionmentioning

confidence: 99%

Selective nitration of calix[4]arenes that easily gave inherently chiral calix[4]arenes

Wang

Chen

Zheng

et al. 2014

J Incl Phenom Macrocycl Chem

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Proximally dietherified calix[4]arene at lower rim was selectively nitrated to give mononitrocalix[4]arene, dinitrocalix[4] arene, and trinitrocalix[4]arene,respectively, under different reaction conditions. These three nitrocalix[4]arenes could be purified in good yield just by recrystallization, which provided a concise approach to inherently chiral calixarene. It was disclosed by crystal structure of trinitrocalix[4]arene that R-enantiomer and S-enantiomer of it could form a self-included dimer by NO 2 -HAr hydrogen bond and CH 3 -Pi interaction in the cavity of the calixarene. In the presence of optically pure (1S,2S)-1,2-diphenyl-1,2-ethanediamine, (1R,2R)-1,2-cyclohexanediamine, cinchonidine, or cinchonine, the two enantiomers of trinitrocalix[4]arene could be discriminated by 1 H NMR spectrum.

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Preparation of p-nitrocalix[n]arene methyl ethers via ipso-nitration and crystal structure of tetramethoxytetra-p-nitrocalix[4]arene

Cited by 22 publications

References 12 publications

Facile synthesis of 10‐tert‐butyl[1]benzoxepino[3,4‐b][1,3] dioxolo[4,5‐g]quinolin‐12(6H)‐ones

Facile synthesis of 10‐tert‐butyl[1]benzoxepino[3,4‐b][1,3] dioxolo[4,5‐g]quinolin‐12(6H)‐ones

Mechanism of enhanced oxidation ability of dilute nitric acid and dissolution of pure gold in seawater with nitric acid

Selective nitration of calix[4]arenes that easily gave inherently chiral calix[4]arenes

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