Perfluorocyclopentene → Phenol

HRID 981364

Reaction equation

HRID 981364 reaction equation
[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]

Participants

10

Reactant 4

HCID 11212PerfluorocyclopenteneHCID 24524FluorineHCID 4445035Phenolate SodiumHCID 126333481,2-Bisphenoxy-3,3,4,4,5,5-hexafluorocyclopent-1-ene

Product 3

HCID 996PhenolHCID 86632-NaphtholHCID 12767Hexafluorocyclobutene

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolventHCID 8471TriethylamineSolvent

Procedure

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).

Workup

  1. custombe concluded that this reaction

Sources & evidence

ORD record
ord-8b189d6b195749a2befcd5b4bed5f57f
Source dataset
uspto-grants-1991_02
Patent number
US04990633

Linked notes

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