277. Organic fluorine compounds. Part X. Reaction of organic compounds with iodine in the presence of silver fluoride or trifluoroacetate

Bergmann, Ernst D.; Shahak, Israël

doi:10.1039/jr9590001418

Cited by 13 publications

(33 citation statements)

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“…2b, confirmed that this compound had the D-gluco configuration (large z icinal couplings of ca. 9 Hz between H-2, H-3; H-3, H-4; and H-4, H-5) and confirmed the a-configuration at C-1 (J,*, = 2.5 Hz). On this basis, C has the structure 2-broino-2-deoxy-cr-D-glucopyranosyl fluoride triacetate.…”

Section: Resultsmentioning

confidence: 58%

“…It is particularly significant that the conversion of 6 to 3 does not lead to the formation of any of the -ic-anomer, which is formed, in ca. 9 %yield, during the "XF" addition reaction itself. This finding inmediately excludes the possibility, which we ha+e thus far ignored, that the "XF" addition itself merely involves the formation of the 1,2-dibromide(s) (18) which subsequently react(s) with the silver fluoride to give the glycosyl fluoride(s).…”

Section: Resultsmentioning

confidence: 99%

“…To characterize further the a-D-manno derivative (2) attempts were made to remove the bromine substituent from G-2 by hydrogenolysis, which should afford the known (19) 2-deoxy-a-Darabino-hexopyranosyl fluoride triacet-ate (9). Although a pure specimen could not be isolated from an atnlospheric hydrogenolysis ipalladium catalyst), it was present in the reaction product to the extent of ca.…”

Section: Resultsmentioning

confidence: 99%

“…Bergmann and Shahak (9) used an excess of cyclohexene as the reaction solvent and characterized the product as 3-iodocyclohex-1-ene. Schmidt and Meinert (10) used acetonitrile as solvent and reported the isolation of trans-2-iodo-cyclohexylfluoride.…”

Section: Introductionmentioning

confidence: 99%

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Studies of specifically fluorinated carbohydrates. Part III. A new method for the addition of the elements of "BrF" and of "IF" to unsaturated carbohydrate derivatives

Hall¹,

Manville²

1969

Can. J. Chem.

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A smooth addition of the elements of "BrF", to D-glucal triacetate (I), occurs when bromine is reacted with 1 in the presence of silver lnonofluoride and a suitable solvent. This reaction affords a major product 2-bron1o-2-deoxy-cr-~-mannopyranosyl fluoride triacetate, together with smaller quantities of 2-bromo-2-deoxy-a-D-glucopyranosyl fluoride triacetate and the corresponding fi-o-anomer. The structures of these products have been elucidated by fluorine and proton magnetic resonance studies, and confirmed by several independent syntheses. The same three products are obtained when "BrF" is generated in situ from N-bromosuccinimide and HF; however, under these conditions 2-deoxya-D-arabino-hexopyranosyl fluoride triacetate is also formed in ca. 7% yield. The Br2/AgF reagent has also been reacted with several 3,4-dihydro-2H-pyran derivatives and with other glycals. In all cases the major product(s) corresponds to the trans addition of "BrF". Similar results are obtained for the addition of the elements of "IF" to all of the above derivatives.

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Section: Resultsmentioning

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Studies of specifically fluorinated carbohydrates. Part III. A new method for the addition of the elements of "BrF" and of "IF" to unsaturated carbohydrate derivatives

Hall¹,

Manville²

1969

Can. J. Chem.

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“…The 2,3-hexancdionc used as internal standard was synthesized by the method of Bergmann et al 3 The diketones formed were isolated from the reaction products by precipitation with 2,4-dinitrophenylhydrazine. The free diketones were liberated from the 2,4-dinitrophenylhydrazones by distillation over 50% sulphuric acid.…”

Section: Methodsmentioning

confidence: 99%

A Semi-Automatic Method for the Gas Chromatographic Determination of Vicinal Diketones in Alcoholic Beverages

Leppänen¹,

Ronkainen²,

Koivisto³

et al. 1979

Journal of the Institute of Brewing

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A method has been developed for the routine determination of diacetyl and pentanedione in alpoholic beverages. After the addition of internal standard and any necessary dilution, a stream of nitrogen swept the components of the sample at a fixed temperature to a 2 ml injection loop of a gas chromatograph fitted with an electron capture detector. The data from the chromatograph were collected on cassette and processed by computer. The time between starting tempera ture equilibration of the sample and obtaining the diketone content as /ig/litre beverage was about 17 min. The coefficient of variation for diacetyl was 1 -8% (5-1%, with manual injections) and for 2,3 pentanedione 1 6% (91%) for replicated analyses of the same sample.

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Iodine-Silver(I) Fluoride

Brisbois

Wanke

2001

Encyclopedia of Reagents for Organic Synthesis

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277. Organic fluorine compounds. Part X. Reaction of organic compounds with iodine in the presence of silver fluoride or trifluoroacetate

Cited by 13 publications

References 0 publications

Studies of specifically fluorinated carbohydrates. Part III. A new method for the addition of the elements of "BrF" and of "IF" to unsaturated carbohydrate derivatives

Studies of specifically fluorinated carbohydrates. Part III. A new method for the addition of the elements of "BrF" and of "IF" to unsaturated carbohydrate derivatives

A Semi-Automatic Method for the Gas Chromatographic Determination of Vicinal Diketones in Alcoholic Beverages

Iodine-Silver(I) Fluoride

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