Aluminum nitrate and silica sulfuric acid as efficient nitrating media for the mononitration of phenols under mild and heterogeneous conditions

Abstract

A variety of phenol derivatives were successfully nitrated via combination of Al(NO 3 ) 3 Á9H 2 O and silica sulfuric acid in the presence of wet SiO 2 (50% w/w) in dichloromethane at room temperature with moderate-to-good yields.Résumé : Opérant à la température ambiante, dans le dichlorométhane et faisant appel à une combinaison de Al(NO 3 ) 2 Á9H 2 O et d'acide sulfurique lié à de la silice, en présence de SiO 2 humide (50 % w/w), on a réalisé avec succès la nitration des dérivés du phénol, avec des rendements allant de modérés à bons. Mots-clés : nitration, phénol, conditions hétérogènes, nitrate d'aluminium [Al(NO 3 ) 2 Á9H 2 O], acide sulfurique lié à de la silice (SiO 2 -OSO 3 H). [Traduit par la Rédaction]

Solid-Phase Aromatic Nitration with Mg(NO<sub>3</sub>)<sub>2</sub> on Silica Gel

“…1 H NMR (400 MHz) and 13 C NMR (100 MHz) spectra were taken with a Bruker AV 400M spectrometer for CDCl 3 solution using SiMe 4 as an internal standard. High-resolution mass spectra (HRMS) were measured on a Thermo Scientific Q Exactive mass spectrometer equipped with an electrospray ionization source.…”

“…Also, Bi(NO 3 ) 3 [10] and NaNO 2 [11] were used as reagents for indirect nitration in solution phase. Thus solid-phase nitration using nitrate salts such as Bi(NO 3 ) 3 , Al(NO 3 ) 3 ·9H 2 O [12] [13] and Zn(NO 3 ) 2 on silica gel has been reported so far.…”

Green and Metal-free Catalytic Oxidation of Urazoles into Triazolinediones by Guanidinium Nitrate and Catalytic Amounts of Silica Sulfuric Acid

“…21,27 The critical point of this mechanism is auto ionization of nitric acid, which generates in situ nitronium ion (NO2 + ). Surprisingly, when a urazole with activated aromatic moiety (for example 4-methoxyphenyl urazole) was subjected to oxidation reaction with described system, 4-(4-methoxyphenyl)-1,2,4-triazole-3,5-dione was selectively produced and no nitrated product was observed (Table 1 entry 5 and Scheme 3).…”

“…In continuation of our studies on the application of new reagents in organic functional group transformations [14][15][16][17][18][19][20][21][22][23] we became interested to introduce a metal-free catalytic media for the conversion of 4-substituted urazoles into triazolinediones by mixing of guanidinium nitrate and catalytic amounts of silica sulfuric acid.…”

Versatile and Efficient Conversion of Thiols into Disulfides by Poly(4-vinylpyridinium tribromide) as Reusable Oxidizing Polymer

“…In continuing of our attempts to introduce new methodologies for organic functional group transformations, [28][29][30][31][32][33][34][35][36] we became interested to prepare a new and recoverable polymeric tribromide reagent. Therefore we decided to prepare poly(4-vinylpyridinium tribromide) from poly (4-vinylpyridin) as is outline in Scheme 1.…”