- THE PREPARATION AND REACTIONS OF 1,3,4,5,6,7,8-HEPTAFLUORO-2-NAPHTHYL PROP-2-ENYL ETHER: FORMATION OF 1,3,4,5,6,7,8-HEPTAFLUORO-1-(PROP-2-ENYL)NAPHTHALEN-2-ONE AND THE PHOTOLYSIS AND PYROLYSIS OF THIS KETONE
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1,3,4,5,6,7,8-Heptafluoro-2-naphthyl prop-2-enyl ether (8) was isomerised in boiling xylene to 1,3,4,5,6,7,8-heptafluoro-1-(prop-2-enyl)naphthalen-2-one (9).Photolysis of (9) gave 2,5,7-trifluoro-3,4-(tetrafluorobenzo)tricyclo2,7>non-3-en-6-one (11) (by a addition) and 1,2,7-trifluoro-3,4-(tetrafluorobenzo)tricyclo2,7>non-3-en-8-one (12) (via an initial photochemically-allowed sigmatropic shift).Pyrolysis of (9) at 455 deg C also gave (11), while at 490 deg C, both (9) and (11) gave 1-fluorovinyl 4,5,6,7,8-pentafluoro-1-naphthyl ketone (19).
- Brooke, Gerald M.,Matthews, Raymond S.,Robson, Nigel S.
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- Method of making chlorofluoroethers
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A method is provided for preparation of chlorofluoroethers ClCF2CFClOR8f and Cl2CFCFClOR8f by direct fluorination of Cl2CHCH2OR8 and Cl3CCH2OR8, respectively, wherein R8 is a C1-C20 alkyl-or acyl-containing group optionally up to 5 ether oxygen atoms and optionally substituted by functional groups and R81, is the corresponding perfluoroalkyl or perfluoracyl-containing group.
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- REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. II. NUCLEOPHILIC SUBSTITUTION IN NITROHALOGENO AND POLYFLUORINATED AROMATIC COMPOUNDS
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The possibility of aromatic nucleophilic substitution in liquid ammonia was investigated for the case of the reaction of p-nitrochlorobenzene, 2,4-dinitrochlorobenzene, hexafluorobenzene, bromopentafluorobenzene, pentafluorobenzene, and octafluoronaphthalene with a series of charged nucleophiles (potassium hydroxide and sulphite, alcoholates, sodium azide, thiophenolate, phenolate, and sulfide) at -70 to -33 deg C.It was shown that alkyl ethers of p-nitrophenol, phenyl p-nitrophenyl sulfide, 2,4-dinitrophenyl azide, polyfluorinaqted phenols, and their ethers can be obtained with good yields.Comparisons of the results with published data on the rate of the same reactions in other solvents shows that liquid ammonia is highly effective as a solvent for aromatic nucleophilic substitution reactions and in some cases makes it possible to avoid side processes.
- Shtark, A. V.,Kizner, T. A.,Shteingarts, V. D.
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p. 2051 - 2056
(2007/10/02)
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