Fluoroorganic compounds

Knunyants and G.G. Yokobsen, Synthesis of Fluoroorganic Compounds, Springer-Verlag, Berlin, Heidelberg, New York Tokyo, 1985. 

Fluorination by Sulphur Tetrafluoride, Organic Reactions, Vol. 34, Ed. A.S.Kende, John Wiley and Sons New York, 1985. 

Narayana and M. Periasamy, Organic Synthesis via Carbonylation of Organometallic Reagents with Carbon Monoxide, Synthesis, 1985, 253. 

Lanthanides in Organic Synthesis, Aldrichimica Acta. 1985, 18, 87. 

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The Application of Thermolytic Reactions for the Syntheses of Fluoroorganic Compounds Platonov, V C Yakobson, G G Svnthesis 374-384 88... 

Although the spectra of fluorine containing compounds are non-exceptional, other than for the F—H coupling, and are highly predicable, typical proton chemical shift and coupling constant data will be provided within each chapter for each class of fluoroorganic compound. 

While on the subject of fluoroorganic compounds, one cannot overstate the importance of fluoropolymers in modem industry and science. There is hardly anyone around today who has never heard of polytetrafluoroethylene (PTFE) [CF2—CF2] . Housewives who know nothing about fluorine use PTFE-coated frying pans or pots, and know that PTFE makes washing up easier, because virtually nothing sticks to a PTFE-coated utensil. 

Xenon difluoride reacts with carbon-carbon single, double, and triple bonds giving addition fluoroorganic compounds, e.g.,... 

In this, the adsorbed organic substrate is electrochemically oxidised to form a radical cation, a proton is eliminated in a chemical step to form a radical, which is then further electrochemically oxidised to a carbocation, which reacts with a fluoride ion in the double layer to produce the fluoroorganic compound. 

I. L. Knunyants and G. G. Yakobson, Syntheses of Fluoroorganic Compounds, Springer-Verlag, Berlin (1985), pp. 196-197 [Original paper G. G. Furin, S. A. Kurupoder, and G. G. Yakobsen, Ilpy. Sib. Otd. Akad. Nauk. SSSR Ser. Khim. Nauk 5, 146 (1976) (in Russian)]. 

The Application of Thermolytic Reactions for the Syntheses ol Fluoroorganic Compounds... 

Tetr 34 3 (1978) (Introduction of Fluorine into Organic Molecules Why and How) 47 5329 (1991) (The Combination of Hydrogen Fluoride with Organic Bases as Fluorination Agents) 49 9385 (1993) (Synthesis of Chiral and Bioactive Fluoroorganic Compounds)... 

Reviews on Heteroatom Chemistry 12 211 (1995) (Asymmetric Synthesis of Fluoroorganic Compounds)... 

Hopefully, this book will work both to provide an introduction to the novice and as a resource for those chemists who are more experienced in working with fluoroorganic compounds. As you will soon notice, the book has not been written by an NMR specialist, but rather has been written for working organic chemists by a working organic chemist. 

A wide range of fluorinated compounds are applied as pharmaceuticals and agrochemicals. Several stereoselective methods are used for synthesis of optically active molecules bearing a C-F bond at the stereogenic carbon atom [72, 73]. These are mainly based on diastereoselective fluorination of chiral molecules or enantioselective alkylation of fluoroorganic compounds. Asymmetric introduction of a fluorine... 

G. G. Furin and K.-W. Chi, Synthesis methods for fluoroorganic compounds , p. 400, University of Ulsan Press, Ulsan, Korea (2001). 

P. V. Ramachandran and H. C. Brown, Asymmetric Syntheses of Fluoroorganic Compounds via Chiral Organoboranes, in Asymmetric Fluoroorganic Chemistry , ACS Symposium Series 746, eds. P. V. Ramachandran, and H. C. Brown, American Chemical Society, Washington, DC, 2000, p. 22. 

A wide variety of other alcohol substrates has been resolved, including aryl substituted secondary alcohols, - a-alkyl-P-hydroxy esters, P-hydroxy nitriles, and fluoroorganic compounds. Active chloroacetate esters are commonly used to speed up the hydrolysis reactions, as exemplified in eq 2 Primary acyclic alcohols possessing a stereogenic center that have been resolved include 2,3-epoxy alcohols, - 2-amino alcohols, and crown ethers. ... 

The electrochemical oxidations of several fluorinated amines have been investigated with a view to synthesizing fluoroorganic compounds [272]. Substitution of the hydrogen on the carbon of amines by chloromethyl and fluoromethyl groups slightly increases their oxidation potential [273]. Anodie oxidation of fluoromethyl... 

Soloshonok, V. A. (1999) Enantiocontrolled Synthesis of Fluoroorganic Compounds — Stereochemical Challenges and Biomedicinal Targets, John Wiley Sons, Inc., New York. 

For reviews see. (a) Welch, J. T. (1987) Tetrahedron report number 221 Advances in the preparation of biologically active organofluorine compounds. Tetrahedron, 43, 3123-3197. (b) Resnati, G. (1993) Synthesis of chiral and bioactive fluoroorganic compounds, Tetrahedron, 49, 9385-9445. (c) Soloshonok, V. A. (ed.) (1999) Enantiocontrolled Synthesis of Fluoroorganic Compounds Stereochemical Challenges and Biomedicinal Targets, John Wiley Sons, Ltd, Chichester, UK. (d) Rosen, T. C., Yoshida, S., Kirk, K. L. and Haufe, G. (2004) Fluorinated phenylcyclopropylamines as inhibitors of monoamine oxidases. ChemBioChem., 5, 1033-1043. 

The quest for methods of synthesizing chiral fluoroorganic compounds is one of the most fascinating topics in modern organofluorine chemistry because the replacement of hydrogen with a fluorine atom often results in a significant improvement in the physicochemical properties and biological activities of the molecules. 

Although fluorine itself is the most reactive of all elements, some fluoroorganic compounds have chemical inertness like that of the noble gases. They sometimes cause ecological problems not because of their reactivity but because of the lack it, making them persistent in nature on a geological time scale. 

I. C. Knunyants, G. G. Yakobson, Syntheses of Fluoroorganic Compounds, Springer, 1985. 

Because of the hazardous character of hydrofluoric acid and the difficult access to elemental fluorine itself, the development of organofluorine chemistry and the practical use of fluoroorganic compounds started relatively late in the 19th century (Table 1.1). The real breakthrough was the first synthesis of elemental fluorine by H. Moissan in 1886 [1]. 

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