Perfluorocyclopentene → Phenol

HRID 981364

Reaktionsgleichung

Reaktionsgleichung von HRID 981364
[O:1](C1C(F)(F)C(F)(F)C(F)(F)C=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-][C:27]1[CH:32]=CC=[CH:29][CH:28]=1.[Na+].FC1(F)[C:39]([F:40])=[C:38]([F:41])[C:37]([F:43])([F:42])[C:36]1([F:45])[F:44].FF>COCCOC.CCOCC.C(N(CC)CC)C>[C:2]1([OH:1])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]1[C:24]2[C:23](=[CH:32][CH:27]=[CH:28][CH:29]=2)[CH:22]=[CH:21][C:20]=1[OH:19].[F:43][C:37]1([F:42])[C:38]([F:41])=[C:39]([F:40])[C:36]1([F:44])[F:45]

Komponenten

10

Edukt 4

HCID 11212PerfluorocyclopenteneHCID 24524FluorineHCID 4445035Phenolate SodiumHCID 12633348HCID 12633348, Verbindung

Produkt 3

HCID 996PhenolHCID 86632-NaphtholHCID 12767Hexafluorocyclobutene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

The substitution of both vinylic halogen atoms in dihaloperfluoroalkenes by phenols or by phenoxides is as yet illustrated by a single example: under specific conditions (-40° C., mmol scale, complicated distillation) 1,2-bisphenoxy-3,3,4,4,5,5-hexafluorocyclopent-1-ene could be prepared in 76% yield from sodium phenoxide and octafluorocyclopentene in ethylene glycol dimethyl ether (see J.O.C. 45, 4429 (1980). Based on the other existing literature (for example Fluorine in Organic Chemistry, Wiley, 1973), it could not be concluded that this reaction could underlie a generally applicable synthesis principle. Thus, only monoaryloxy-perfluorocyclobutenes were obtained by reaction of phenol or 2-naphthol with hexafluorocyclobutene in ether using equimolar amounts of triethylamine (see J.A.C.S. 72, 4480 (1950).

Aufarbeitung

  1. custombe concluded that this reaction

Quellen und Nachweise

ORD-Eintrag
ord-8b189d6b195749a2befcd5b4bed5f57f
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990633

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