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Cyclopentadiene → 2,3-Epoxy-5-(perfluorohexyl)bicyclo[2.2.1]heptane

HRID 1729111
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1729111
[F:1][C:2]([F:21])([C:5]([F:20])([F:19])[C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH:3]=[CH2:4].[CH:22]1[CH2:26][CH:25]=[CH:24][CH:23]=1.C([O:31]O)CCC>C1(C)C=CC=CC=1>[O:31]1[CH:22]2[CH:23]1[CH:24]1[CH2:25][CH:26]2[CH:3]([C:2]([F:21])([F:1])[C:5]([F:19])([F:20])[C:6]([F:17])([F:18])[C:7]([F:15])([F:16])[C:8]([F:13])([F:14])[C:9]([F:12])([F:11])[F:10])[CH2:4]1
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Komponenten

5

Edukt 3

HCID 7612CyclopentadieneHCID 91384(Perfluorohexyl)ethyleneHCID 123219n-Butylhydroperoxide

Produkt 1

HCID 190136962,3-Epoxy-5-(perfluorohexyl)bicyclo[2.2.1]heptane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

103 g (250 mmol) of the Diels-Alder reaction product of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octene (perfluorohexylethene) and cyclopentadiene are mixed in 10 ml of dry toluene with 815 mg (2.5 mmol) of molybdenum acetylacetonate, and 104 ml of a 3.6 molar solution oft-butyl hydroperoxide in toluene (375 mmol) are added dropwise at 25° C. within 50 minutes. During this time, the temperature rises to 45° C. The solution is then held at 60° C. for 24 hours, after which the solvent, t-butanol and any remaining t-butyl hydroperoxideis distilled off in a rotary evaporator under reduced pressure. The residueis filtered over silica gel, followed by washing with two 10 ml portions oftoluene. In the course of the distillation over a packed column 15 cm long which is packed with 4 mm glass rings, the product distils at a pressure of 350 mbar and a boiling point of 54° to 56° C.

Aufarbeitung

  1. additionare added dropwise at 25° C. within 50 minutes
  2. customrises to 45° C
  3. distillationafter which the solvent, t-butanol and any remaining t-butyl hydroperoxideis distilled off in a rotary evaporator under reduced pressure
  4. filtrationThe residueis filtered over silica gel
  5. washby washing with two 10 ml portions oftoluene
  6. distillationIn the course of the distillation over a packed column 15 cm long which
  7. customthe product distils at a pressure of 350 mbar

Quellen und Nachweise

ORD-Eintrag
ord-c476122f3ab744c7a8d7624eaf0500b0
Quelldatensatz
uspto-grants-1994_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05331084

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