Formation of nitrate esters in thallium(III) nitrate oxidation of alkenes

Bertsch, Robert; Ouellette, Robert J.

doi:10.1021/jo00932a017

Cited by 12 publications

(4 citation statements)

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“…Pinacol monomethyl ether (A) was prepared by a modified version of the published procedure for 1-methoxy-2-decanol . 2,3-Dimethyl-2,3-epoxybutane (tetramethyloxirane) (1.196 g, 11.96 mmol) was dissolved in CH 3 OH (10 mL).…”

Section: Methodsmentioning

confidence: 99%

Aerobic Oxidation of Lignin Models Using a Base Metal Vanadium Catalyst

et al. 2010

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Dipicolinate vanadium(V) complexes oxidize lignin model complexes pinacol monomethyl ether (A), 2-phenoxyethanol (B), 1-phenyl-2-phenoxyethanol (C), and 1,2-diphenyl-2-methoxyethanol (D). With substrates having C-H bonds adjacent to the alcohol moiety (B-D), the C-H bond is broken in pyridine-d(5) solvent, yielding 2-phenoxyacetaldehyde from B, 2-phenoxyacetophenone from C, and benzoin methyl ether from D. In DMSO-d(6) solvent the reaction is slower, and both C-H and C-C bond cleavage products are observed for D. The vanadium(IV) products of these reactions have been identified and characterized. Catalytic oxidation of C and D has been demonstrated using air and (dipic)V(O)O(i)Pr. For both substrates, the C-C bond between the alcohol and ether groups is broken in the catalytic oxidation. 1-Phenyl-2-phenoxyethanol is oxidized to a mixture of phenol, formic acid, benzoic acid, and 2-methoxyacetophenone. The products of oxidation of 1,2-diphenyl-2-methoxyethanol depend on the solvent; in DMSO benzaldehyde and methanol are the major products, while benzoic acid and methyl benzoate are the major products obtained in pyridine solvent. Phenyl substituents on the model complex facilitate the oxidation, with relative rates of oxidation D > C > B.

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Section: Methodsmentioning

confidence: 99%

Aerobic Oxidation of Lignin Models Using a Base Metal Vanadium Catalyst

et al. 2010

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“…Predominantly southwesterly winds reach the off-town university campus that can be characterized as a rural sampling site partly influenced by urban air masses and the traffic on the parking lots around the campus. [Bertsch and Ouellette, 1974] or by radical nitration of alkyl mononitrates with NO/O2 . Hydroxy alkyl nitrates were prepared by the addition of nitric acid to epoxides [Nichols et al, 1953] If possible, quantitative standards were prepared by weighing and dissolving the organonitrates in organic solvents (e.g., hexane) after liquid chromatographic cleanup.…”

Section: Sampling Locationmentioning

confidence: 99%

“…Mononitrates and most of the dinitrates were prepared by esterification of alcohols with mixed acid (nitric acid and sulfuric acid 1:1) or NO2BF4 in dichloromethane, respectively IOlab et al, 1978IOlab et al, , 1989]. The majority of the dinitrates was synthesized by the reaction of olef'ms with thallium-(III)-nitrate in pentane [Bertsch and Ouellette, 1974] or by radical nitration of alkyl mononitrates with NO/O2 . Hydroxy alkyl nitrates were prepared by the addition of nitric acid to epoxides [Nichols et al, 1953] If possible, quantitative standards were prepared by weighing and dissolving the organonitrates in organic solvents (e.g., hexane) after liquid chromatographic cleanup.…”

Section: Synthesis Of Reference Substancesmentioning

confidence: 99%

Levels and pattern of alkyl nitrates, multifunctional alkyl nitrates, and halocarbons in the air over the Atlantic Ocean

Fischer¹,

Kastler²,

Ballschmiter³

2000

J. Geophys. Res.

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“…^ 4-prR 4-6o bo is the intercept of the equation, and pr and pr are the regression coefficients. F and R are contributions arising from field and inductive effects, taken together, and resonance effects, respectively.9 (9) C. G. Swain and E. C. Lupton, J.…”

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confidence: 99%