Synthesis hypofluorite

Selenium-containing donors, synthesis and manufacture of, 22 212 Selenium dichloride, 22 75t Selenium diethyldithiocarbamate, 22 73t Selenium dioxide, 22 73t, 75t, 88 toxicify of, 22 95 Selenium disulfide, 22 73t Selenium hexafluoride, 22 75t, 87 toxicify of, 22 96 Selenium hypofluorite, 22 75t Selenium iodides, 22 87 Selenium monobromide, 22 75t, 88 Selenium monochloride, 22 75t, 87 in selenium recovery, 22 85 Selenium monoxide, 22 88 Selenium oxidation, selenium recovery via, 22 81-83... 

C.Y. Shiue, P.A. Salvadori, A.P. Wolf, A new synthesis of 2-deoxy-2-[ F]fluoro-D-glucose from F-labeled acetyl hypofluorite, J. Nucl. Med. 23 (1982) 899-903. 

These compounds can be prepared by using either classical processes for synthesis of amino acids (starting from the ad hoc precursor bearing fluorine on the aromatic moiety) or electrophilic fluorination of the arene moiety (e.g., elemental fluorine, xenon fluoride, acetyl hypofluorite). Although these methods are often poorly regioselective, they are useful for the preparation of F labeled molecules used in PET, for example, F tyrosine and dihydrophenylalanine (L-Dopa). ... 

C1F 54.46 - 155.6/- 100.1 + + + + also usable for synthesis of hypofluorites and oxidative S- or Se-fluorinations of organic sulfur and selenium compounds, frequently in situ preparation of the agent from A -chloro-substituted amides and HF, HF-containing systems or AgF 4, 7... 

A preparative solid- gas phase synthesis of acetyl hypofluorite (1, R = Me) has been described it is based on the reaction of dilute fluorine (with air or nitrogen) with a solid complex of potassium acetate with acetic acid and can be also modified7 -9 for the preparation of acetyl... 

The first direct synthesis of 5-fluorocytosine (15) was reported by Robins and Naik,21 in which cytosine (20) was reacted with trifluoromethyl hypofluorite followed by decomposition of the resulting adduct to provide 5-fluorocytosine in 85% yield. Some years later, Takahara disclosed that 15 could be prepared as its hydrofluoride salt in high purity when cytosine was reacted with fluorine gas in the presence of hydrogen fluoride, followed by treatment with methanol.22... 

Trifluoromethyl hypofluorite gained its initial popularity, however, from its reactions with enol derivatives. Such reactions continued to be important during the last decade. The synthesis of complex molecules such as fluoroerythromycin (equation 137)244 and 2-fluoro (25)245 and 16-fluoroestradiols (26) (equation 138)246 are good examples of using CF3OF to produce compounds with useful therapeutic properties. 

Rozen and coworkers30 have also reported that acetonitrile can replace trichlorofluoromethane in the preparation and in situ reactions of acetyl hypofluorite without sacrificing the efficiency and the regio- and stereoselectivity of the addition of AcOF to olefins. Most other solvents investigated proved to be unsatisfactory for the synthesis of AcOF, despite the fact that fluorine does react with the dispersed sodium acetate present in the solvent. 

The fluorination and stereochemistry of the reaction of pyranoid and furanoid glycals with acetyl hypofluorite are described41. In related work42 the synthesis of 2-deoxy-2-fluoro-D-galactapyranose by treatment of 2-deoxy-D-galactapyranose with acetyl hypofluorite is described and the 18F-labelled product was similarly prepared through the use of Ac018F. 

Pentafluorosulfanyl hypofluorite adds readily to a number of alkenes to give only one product, containing the components SF50 and F (77, 78). Because of its facile synthesis, some use is made of SF5OF in electrophilic fluorination (79). The gas-phase structure of SF5OF is reported (SO). 

Bicyclomycin rearrangement product, synthesis, 57, 224 2,2 -Bifuran, 5,5 -dibromo-, 57, 306 2,2 -Biimidazoles bromination, 57, 350 chlorination, 57, 347 2,2 -Biindolyl, synthesis, 56, 174 l,l -Biisoquinoline. formation from isoquinoline and LDA, 56, 245 fiimanes, fluorination by acetyl hypofluorite, 59, 4 Biological properties of heterocyclic betaines and precursors, 60, 250-1... 

Fluorination of aryltrimethylsilanes with xenon difluoride is a method for the synthesis of F-labelcd eompounds, since [ F]XeF2 be prepared. F-Labeled aryl fluorides are also prepared by reaction of aryltrimethylsilanes with F-labeled acetyl hypofluorite and elemental fluorine. ... 

Tris(2,4-pentanedionato)molybdenum(III), synthesis 39 Potassium tetraoxalatouranate(IV), synthesis 40 Trifluoromethyl hypofluorite, synthesis 42 Bis(ethylenediamine)dioxorhenium(V) chloride, bis(ethylene-diamine)oxohydroxorhenium(V) perchlorate, and bis(ethyl-enediamine)dihydroxorhenium(V) hexachloroplatinate(IV), synthesis 44... 

Time-consuming work-up procedures must be avoided in the synthesis of labeled diagnostics, but essentially the usual fluorination methods are used. [1 F]FDG can be prepared by electrophilic fluorination of a glycal with [ F acctyl hypofluorite [87] (Scheme 4.40). This reagent again is produced by reaction of F labeled fluorine gas with KOAc -2HOAc [88]. The synthesis of other [ F]fluor-odopa isomers is illustrated in Scheme 4.41. 

N-Acetylneuraminic acid aldolase, use in fluorinated sugar synthesis, 158,161/ Acylation-hydrolysis of ylides, 2-fluoro-2-oxoalkanoate synthesis, 96-100 Acyl hypofluorites applications, 58 applications for shorter chain homologues, 60,61/ chemistry, 58—61... 

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