Sunlight Oxidation of Alkyl Aryl Tellurides to the Corresponding Carbonyl Compounds: A New Carbonyl Precursor

Ouchi, Akihiko; Hyugano, Takeshi; Liu, Chuanxiang

doi:10.1021/ol901943f

Cited by 23 publications

(11 citation statements)

References 35 publications

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“…19 F NMR was used to study compound 10 using a trifluoroacetic acid internal standard while 1 H NMR was used to study the degradation of compound 11 using the DMSO-d 5 internal standard. To further validate these compounds as potential MC mass tags, the stability was also studied in a buffered aqueous solution by dissolving the compounds in a 50/50 solution of DMSO-d 6 /PBS-d buffer.…”

Section: Stability In Pbs Buffermentioning

confidence: 99%

Organotellurium scaffolds for mass cytometry reagent development

et al. 2015

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Mass cytometry (MC) is a powerful tool for studying heterogeneous cell populations. In previous work, our laboratory has developed an MC probe for hypoxia bearing a methyl telluride mass tag. The methyl telluride was unoptimized, displaying stability and toxicity limitations. Here, we investigate three classes of organotelluriums as MC mass tags: methyl tellurides, trifluoromethyl tellurides and 2-alkyl-tellurophenes. NMR was used to compare the stability of these compounds in aqueous and organic solutions and the compounds were analysed for toxicity in Jurkat cells. The methyl tellurides were moderately stable to aerobic oxidation in organic solution under dry ambient conditions. The trifluoromethyl tellurides were stable to aerobic oxidation in organic solution but decomposed in aqueous solution. The 2-alkyl-tellurophenes proved to be stable in both organic and aqueous solutions under ambient conditions and showed limited toxicity (IC50 > 200 μM) in cell based assays. The synthetic feasibility, chemically stability, and limited toxicity of tellurophenes suggests these groups will be good choices for MC reagent development.

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Section: Stability In Pbs Buffermentioning

confidence: 99%

Organotellurium scaffolds for mass cytometry reagent development

et al. 2015

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“…Nowadays we know that the bad smell of the organotelluro compounds is not a rule. 17 The instability of the organotellurides to the light and air is better understood, 18 and now chemists are able to manipulate them safely.…”

Section: Telluriummentioning

confidence: 99%

Selenium and tellurium chemistry: historical background

Comasseto¹

2010

J. Braz. Chem. Soc.

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“…All this results indicates that the processes must be mediated by one or more radicalar steps [2] . On the other hand radical tellurides derivatives have considerable potential for use in organic synthesis [4,5] . In this work, is shown the first results of the synthesis of a 2-oxazoline telluride derivative and its photo-degradation behavior.…”

Section: Introductionmentioning

confidence: 99%