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Makarov, R. I.; Dubov, I. R.; Lukashin, S. A.

doi:10.1023/a:1007173816522

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“…The nitroxide is prepared from bistrifluoromethylhydroxylamine [283] by reaction with, for example, silver oxide [284] ( Figure 8.111) or potassium permanganate [285]. The nitroxide is prepared from bistrifluoromethylhydroxylamine [283] by reaction with, for example, silver oxide [284] ( Figure 8.111) or potassium permanganate [285].…”

Section: Bistrifluoromethyl Nitroxidementioning

confidence: 99%

Functional Compounds Containing Oxygen, Sulphur or Nitrogen and their Derivatives

Chambers

2004

Fluorine in Organic Chemistry

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This chapter contains only a brief survey of the chemistry of a range of derivatives that are of interest to the organic chemist; further aspects have been discussed in detail and may be referred to elsewhere [1,2]. Because of the extreme electronegativity of fluorine and fluorocarbon groups, the acidities of various functions are increased by introduction of these groups. Some examples are given in Table 8.1: it is clear that fluorocarbon groups have a dramatic effect on the acidities of alcohols and carboxylic acids. Moreover, the CF 3 SO 2 group is one of the most electron-withdrawing groups known [3] and consequently the carbon acid ðCF 3 SO 2 Þ 2 CH 2 is more acidic than trifluoroacetic acid. Also, the sulphonamide ðCF 3 SO 2 Þ 2 NH is a strong acid [4].Conversely, fluorine or fluorocarbon groups have a major effect in reducing the base strength of amines, ethers and carbonyl compounds; for example, 2,2,2-trifluoroethylamine (pK b ¼ 3:3) is ca. 10 5 times less basic than ethylamine. Also, pentafluoropyridine is only protonated in strong acid [6], whereas hexafluoroacetone is not protonated even in superacids [7-9] and perfluorinated tertiary amines and ethers are sufficiently non-basic for them to be used as inert fluids interchangeably with perfluorocarbons.

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Section: Bistrifluoromethyl Nitroxidementioning

confidence: 99%

Functional Compounds Containing Oxygen, Sulphur or Nitrogen and their Derivatives

Chambers

2004

Fluorine in Organic Chemistry

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show abstract

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Cited by 1 publication

References 2 publications

Functional Compounds Containing Oxygen, Sulphur or Nitrogen and their Derivatives

Functional Compounds Containing Oxygen, Sulphur or Nitrogen and their Derivatives

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