Pyridine dichromate

Pyridine compounds, 22 91-92, 116 prices of, 22 116 Pyridine derivatives, 22 91, 112 acute toxicology of, 22 118 formation of, 22 109, 111 Pyridine dichromate... 

Pyridine, 48, 50, 65, 68, 164, 168, 197, 221, 260, 290, 296, 308 2-Pyridine aldehyde, 161 Pyridine aldehydes, 161 Pyridine—Borane, 299 Pyridine-2-carboxylic acid, 16 Pyridine dichromate, 239 Pyridine hydrochloride, 31, 239—240 Pyridinium bromide perbromide, 111, 131 2-Pyridone, 157 Pyrimidine nucleosides, 197 Pyrrole, 126... 

Oxidizing agent.1 Pyridine dichromate is similar to the Sarett reagent (1, 145-146) but has the advantage that the preparation is relatively safe. It is used in the same way and yields are comparable. 

Dissolve I drop of quinoline in 1 ml. of dil. HCl and add a few drops of a saturated solution of potassium dichromate. A copious orange-yellow precipitate of quinoline dichromate, (C,H7N)2 HjCrj07, is formed pyridine does not give a crystalline dichromate under these conditions. 

Hydroxylamine Barium oxide and peroxide, carbonyls, chlorine, copper(II) sulfate, dichromates, lead dioxide, phosphorus trichloride and pentachloride, permanganates, pyridine, sodium, zinc... 

Pyridine carboxamide [98-92-0] (nicotinamide) (1) and 3-pyridine carboxylic acid [59-67-6] (nicotinic acid) (2) have a rich history and their early significance stems not from their importance as a vitamin but rather as products derived from the oxidation of nicotine. In 1867, Huber prepared nicotinic acid from the potassium dichromate oxidation of nicotine. Many years later, Engler prepared nicotinamide. Workers at the turn of the twentieth century isolated nicotinic acid from several natural sources. In 1894, Su2uki isolated nicotinic acid from rice bran, and in 1912 Funk isolated the same substance from yeast (1). 

This complex, formerly called pyridine perchromate and now finding application as a powerful and selective oxidant, is violently explosive when dry [1], Use while moist on the day of preparation and destroy any surplus with dilute alkali [2], Preparation and use of the reagent have been detailed further [3], The analogous complexes with aniline, piperidine and quinoline may be similarly hazardous [4], The damage caused by a 1 g sample of the pyridine complex exploding during desiccation on a warm day was extensive. Desiccation of the aniline complex had to be at ice temperature to avoid violent explosion [4]. Pyridinium chlorochromate is commercially available as a safer alternative oxidant of alcohols to aldehydes [5], See Chromium trioxide Pyridine Dipyridinium dichromate See Other AMMINECHROMIUM PEROXOCOMPLEXES... 

AW, Acid-washed Choi, Cholesterol DMAP, 4-(Dimethylamino)pyridine DMF, N,/V-Dimethylformamide DMTr, Di(p-niethoxyphenyl)phenyl methyl GalNAc, N-Acetylgalactosamine, 2-acetamido-2-deoxy-D-galactose HMF, 5-Hydroxymethylfur-fural, 5-(hydroxymethyl)-2-furaldehyde INOC, Intramolecular nitrile oxide-alkene cycloaddition Lea, Lewisa Lex, Lewisx MOM, Methoxymethyl MP, p-Methoxyphe-nyl MS, Molecular sieves NIS, N-Iodosuccinimide PCC, Pyridinium chlorochromate PDC, Pyridinium dichromate PMA, Phosphomolybdic acid PMB, p-Methoxybenzyl ... 

A useful method for the synthesis of 1-unsubstituted 2-arylindolizines is provided by the 1,5-dipolar cyclization of pyridinium ylides derived from 181, in the presence of the oxidant tetrakis(pyridine)cobalt(ll) dichromate (TPCD), which oxidizes the intermediate dihydroindolizine 182 (Scheme 43). The study demonstrated that the presence of an aryl group on the double bond was necessary for the reaction to occur. 

Prior to our original report7 on this method, acceptable and general preparative routes to a-iodocycloalkenones had not been described. Treatment of a p-substituted cycloalkenone with trimethylsilyl azide and a mixture of iodine and pyridine sequentially in dichloromethane has now been reported as a method for the preparation of p-substituted-a-iodocycloalkenones.8 The combination of iodine and pyridinium dichromate has also been reported to provide a-iodoenones from enones as well as from ethynyl carbinols.9 10 Some successes have also been achieved with enones and iodine azide (IN3)11 and iodine/ceric ammonium nitrate.12-14 The submitters first variant5 of the present procedure used carbon tetrachloride as a solvent. In this procedure this solvent has been replaced with the more benign diethyl ether. 

Pyridinium dichromate Dichromic acid, compd. with pyridine (1 2) (8) Chromic acid (H2Cr207), compd. with pyridine (1 2) (20039-37-6)... 

The Collins/Sarett oxidation (chromium trioxide-pyridine complex), and Corey s PCC (pyridinium chlorochromate) and PDC (pyridinium dichromate) oxidations follow a similar pathway as the Jones oxidation. All these oxidants have a chromium (VI), normally yellow, which is reduced to Cr(IV), often green. 

Pyridine, methyltrioxorhenium hgands, 460-1 Pyridine-2,6-dicarboxylate (dipic), transition metal peroxides, 1060, 1061 Pyridinium dichromate, alcohol oxidation, 787-8... 

The 1,3-dipolar addition of ylide 223 with various dipolarophilic alkenes to produce 224 after aromatization of the adducts was reported to proceed significantly more selectively in the presence of MnOz than in the original reaction where TPCD (tetrakis(pyridine) cobalt(II) dichromate) was used as the oxidant in which 224 were minor by-products <99JCR(S)552>. 

Acridine is readily oxidized to acridone by sodium dichromate and acetic acid. Pyridin-2-one and nicotinic acid have been found to undergo oxidation to oxalic add on treatment with Fenton s reagent (69CHE563). 

All of the usual chromium-based oxidation reagents that have been used for the oxidation of cyclobutanols to cyclobutanones, for example, chromium(VI) oxide (Jones reagent),302 pyri-dinium chlorochromate,304 pyridinium dichromate,307 and chromium(YI) oxide/pyridine (Collins),303 are reported to do so without any serious problems. Alternatively, tetrapropylam-monium perruthenate in the presence of A-methylmorpholine A -oxide. oxalyl chloride in the presence of triethylamine in dimethyl sulfoxide (Swern),158,309,310 or phenyl dichlorophos-phate in the presence of triethylamine and dimethyl sulfoxide in dichloromethane (Pfitzner-Moffatt),308 can be used. The Pfitzner-Moffatt oxidation procedure is found to be more convenient than the Swern oxidation procedure, especially with respect to the strict temperature control that is necessary to achieve good yields in the latter, e.g. oxidation of 1 to give 2.308... 

The action of H202 on acidic dichromate solutions gives an unstable blue species which can be extracted into ether (equation 128).2,518,1428 On the addition of pyridine the blue compound Crvl0(02)2py crystallizes. The molecules are distorted pentagonal pyramids with sideways-bonded peroxo groups (298) 1429 some workers with less refined data have reported rather different bond distances.1430 In water the blue species is considered to be CrO(62)2(OH2), in ether it is Cr0(02)20Et2, and amines such as aniline, bipy and phen can replace the pyridine. With bidentate bipy the coordination sphere becomes essentially a pentagonal bipyramid (299),... 

The phase-stabilized AN is prepd by mixing 90 parts AN, 10 ps K nitrate some water, heating the mixt to 140°F, drying and grinding to 40 micron size particles. The proplnt is compressed into grains. Example of compn AN 82.95, K nitrate 9.22, petroleum pitch 4.11 90/10 copolymer of l,3-butadiene/2-methyl-5 -vinyl pyridine 1.76 Amm dichromate 1.96%] EE)R.MacDonald A.M.Bedard, "Methods of Chemical Analysis of Cardeplex Propellant No 4760/A5 and Its Ingredients", CARDE TR426/63 (1963) (Cardeplex No 4760/A5 is a composite ammonium perchlorate-polyurethane proplnt. Analysis of fully cured product includes detns of Amm perchlorate, Al, ferric acetylacetonate, phenyl-/3 -naphthylamine, lithium fluoride total iron) FF)Anon,... 

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