Aromatic fluorine compounds

A. E. Pavlath and J. E. Aromatic Fluorine Compounds, Reiohold Publishing Corp., New York, 1962. 

Handbook of Aromatic Fluorine Compounds, Olin Corp., Stamford, Coim., 1976. 

The preparation of aromatic fluorine compounds may be accomplished by direct fluorination or by fluonnation of organometallic intermediates. Tlte ipso fluorination of an aryl organometallic derivative with a positive fluorine reagent allows control over the regioselectivity of the fluorination and offers advantages in the preparation of F-labeled materials [II, 50],... 

Pavlath, A E, Lefffler, A J Aromatic Fluorine Compounds Monograph... 

He has published more than 100 research papers and holds 25 patents. He has written three books, one of them ACS Monograph 155, Aromatic Fluorine Compounds, in 1963. In 1976, he received the ACS California Section Award for Outstanding ConUibution to Chemistry for his work of a quarter century on various aspects of fluorine chemistry. In addition to his scientific activities, he is also serving his second term on the ACS Board nf ri... 

Since the aerobic degradation of halogenated phenols takes place by monooxygenation and is discussed in Part 2 of this chapter, it is not discussed here except to note the production of chlorocat-echols from chlorophenols and chloroanilines. Emphasis is placed on chlorinated substrates, and reference may be made to a review (Allard and Neilson 2003) for details of their brominated and iodinated analogs. The degradation of aromatic fluorinated compounds is discussed in Part 3 of this chapter. 

The physiological effects of the fluoride ion were reviewed by McClure 74) in 1933. Lehmann 72) published an article on the toxicity of aromatic fluorine compounds in 1928. However, it has been impossible to investigate the toxicity of the organofluorine compounds as thoroughly as that of the organochlorine compounds. 

Finger, G. C., Reed, F. H. and Tehon, L. R. (1955). Aromatic Fluorine Compounds as Fungicides. Illinois State Geological Survey. 

Aubagnac, J.-L. Gilles, I. Claramunt, R.M. Escolastico, C. Sanz, D. Elguero, J. Reduction of Aromatic Fluorine Compounds in FAB-MS. Rapid Commun. Mass Spectrom. 1995,9,156-159. 

Balz, G. Schiemann. G. Ber. Dtsch. Chem. Ges. 1927, 60, 1186. Gunther Schiemann was bom in Breslau, Germany in 1899. In 1925, he received his doctorate at Breslau, where he became an assistant professor. In 1950, he became the Chair of Technical Chemistry at Istanbul, where he extensively studied aromatic fluorine compounds. 

Pavlath, A.E. Leffler, A.L. Aromatic Fluorine Compounds Reinhold New York, 1962. 

Pavlath, A E,Lefffler, A J Aromatic Fluorine Compounds Monograph No 155, American Chemical Society Washington, DC, 1962, pp 12-45... 

The order of reactivity of the halogens is F2 > Cl2 > Br2 > 12. Fluorine is too reactive to be of practical use for the preparation of aromatic fluorine compounds and indirect methods are necessary (see Section 23-1 OB). Iodine usually is unreactive. It has been stated that iodination fails because the reaction is reversed as the result of the reducing properties of the hydrogen iodide that is formed ... 

Howdeshell and Hites [102] identified three aromatic fluorinated compounds associated with the production of 4-(trifluoromethyl)-chlorobenzene in sediment core samples from Lake Ontario in 1993. These compounds were specifically associated with the Hyde Park dumpsite near the Niagara River [97], which was also likely to be the main source of 2378-TeCDD (Fig. 9). The average maximum years for concentrations of these fluorinated compounds was 1969-1971 in the Niagara, Mississauga, and Rochester Basins, and 1975 in the Kingston Basin. Pearson et al. [19] noted that the peak PCDF concentration in Lake Ontario sediments corresponded to that of the fluorinated compounds, suggesting that Hyde Park may be the source of the unusual PCDF contamination of Lake Ontario as well as 2378-TeCDD. 

The industrial routes to the synthesis of aromatic fluorine compounds, in which fluorine is directly bonded to an aromatic ring carbon, have been previously reviewed [136], In contrast to the synthesis of aromatic chlorine and bromine compounds, aromatic fluorine-containing molecules require the use of specialized chemical equipment and additional safety precautions. The reason for these measures is the toxicity and corrosive nature of fluorine reagents. 

N. Ishikawa, Aromatic fluorine compounds as intermediates for pharmaceuticals, agrochemicals and dyes, Senryo to Yakuhin 26 (6) (1981) 106-113. 

G. Balz, G. Schiemann, Aromatic fluorine compounds. I. A new method for their preparation, Chem. Ber. 60 (1927) 1186. 

A. Roe, Preparation of Aromatic Fluorine Compounds from Diazonium Fluoroborates The Schiemann Reaction, Org. React. 1949, 5, 193-228. 

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