DE2858263C2 - Halogenated hexa-2,4-dienes and processes for their preparation - Google Patents
Halogenated hexa-2,4-dienes and processes for their preparationInfo
- Publication number
- DE2858263C2 DE2858263C2 DE2858263A DE2858263A DE2858263C2 DE 2858263 C2 DE2858263 C2 DE 2858263C2 DE 2858263 A DE2858263 A DE 2858263A DE 2858263 A DE2858263 A DE 2858263A DE 2858263 C2 DE2858263 C2 DE 2858263C2
- Authority
- DE
- Germany
- Prior art keywords
- udf54
- udf53
- formula
- dienes
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- APPOKADJQUIAHP-UHFFFAOYSA-N hexa-2,4-diene Chemical class CC=CC=CC APPOKADJQUIAHP-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- -1 cyclopropanecarboxylic acid ester Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- FTMCNCGWNJMMQS-UHFFFAOYSA-M 3-methylbut-2-enyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=C(C)C)C1=CC=CC=C1 FTMCNCGWNJMMQS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 description 2
- QAPXLUZMMFIIBI-UHFFFAOYSA-N 1,1,3,3-tetrafluoropropan-2-one Chemical compound FC(F)C(=O)C(F)F QAPXLUZMMFIIBI-UHFFFAOYSA-N 0.000 description 2
- WJUBBUUEZPOAGH-UHFFFAOYSA-N 2-(difluoromethyl)-1,1-difluoro-5-methylhexa-2,4-diene Chemical compound CC(C)=CC=C(C(F)F)C(F)F WJUBBUUEZPOAGH-UHFFFAOYSA-N 0.000 description 2
- BSCUMHLWIBIQDT-UHFFFAOYSA-N CC(C)=CC=C(Cl)C(F)(F)C(F)F Chemical compound CC(C)=CC=C(Cl)C(F)(F)C(F)F BSCUMHLWIBIQDT-UHFFFAOYSA-N 0.000 description 2
- IFCIHMDXICWJFB-UHFFFAOYSA-N ClC(C(=C(C=C(C)C)C(F)F)Cl)(F)F Chemical compound ClC(C(=C(C=C(C)C)C(F)F)Cl)(F)F IFCIHMDXICWJFB-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- QRKKTXWUDLJYCV-UHFFFAOYSA-N 1,3-dichloro-1,1,3,3-tetrafluoropropan-2-one Chemical compound FC(F)(Cl)C(=O)C(F)(F)Cl QRKKTXWUDLJYCV-UHFFFAOYSA-N 0.000 description 1
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/19—Halogenated dienes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/42—Halogenated unsaturated alcohols acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Das deutsche Patent 28 02 962 betrifft Cyclopropancarbonsäureesterderivate der Formel I °=c:80&udf54;&udf53;vu10&udf54;&udf53;vz7&udf54; &udf53;vu10&udf54;in der einer der Substituenten R¹ und R² für eine Gruppe der Formel
W(CF&sub2;) m -
wobei W Wasserstoff, Fluor oder Chlor ist und m den Wert 1 oder 2 hat, steht und der andere für Fluor, Chlor oder Brom oder eine Gruppe der Formel °=c:60&udf54;&udf53;vu10&udf54;&udf53;vz5&udf54; &udf53;vu10&udf54;wobei X, Y und Z unabhängig voneinander Wasserstoff, Fluor oder Chlor sind, steht und R³ Wasserstoff oder eine Cyan- oder Äthinylgruppe bedeutet.German Patent 28 02 962 relates to cyclopropanecarboxylic acid ester derivatives of the formula I °=c:80&udf54;&udf53;vu10&udf54;&udf53;vz7&udf54;&udf53;vu10&udf54;in which one of the substituents R¹ and R² represents a group of the formula
W(CF2) m -
where W is hydrogen, fluorine or chlorine and m is 1 or 2, and the other is fluorine, chlorine or bromine or a group of the formula °=c:60&udf54;&udf53;vu10&udf54;&udf53;vz5&udf54;&udf53;vu10&udf54;where X, Y and Z are independently hydrogen, fluorine or chlorine, and R³ is hydrogen or a cyano or ethynyl group.
Diese Verbindungen besitzen sehr gute insecticide Eigenschaften und eine gute Beständigkeit gegenüber Abbau durch Licht. Durch letztere Eigenschaft unterscheiden sie sich von ähnlichen natürlich vorkommenden Cyclopropancarbonsäurederivaten, von denen seit langem bekannt ist, daß sie insecticide Eigenschaften besitzen.These compounds possess very good insecticidal properties and good stability to photodegradation. The latter property distinguishes them from similar naturally occurring cyclopropanecarboxylic acid derivatives, which have long been known to possess insecticidal properties.
Ein Verfahren, das sich zur Herstellung der in der genannten Patentschrift beschriebenen Verbindungen eignet, besteht darin, daß ein Niederalkylester der Formel II °=c:90&udf54;&udf53;vu10&udf54;&udf53;vz8&udf54; &udf53;vu10&udf54;worin R&sup4; für Niederalkyl mit bis zu 6 Kohlenstoffatomen, vorzugsweise Methyl oder Äthyl, steht und R¹ und R² die oben angegebenen Bedeutungen besitzen, mit einem Alkohol der Formel III °=c:50&udf54;&udf53;vu10&udf54;&udf53;vz4&udf54; &udf53;vu10&udf54;zur Bewirkung einer Umesterungsreaktion erhitzt wird.A process suitable for preparing the compounds described in the cited patent specification comprises heating a lower alkyl ester of the formula II °=c:90&udf54;&udf53;vu10&udf54;&udf53;vz8&udf54;&udf53;vu10&udf54;wherein R⁴ is lower alkyl having up to 6 carbon atoms, preferably methyl or ethyl, and R¹ and R² have the meanings given above, with an alcohol of the formula III °=c:50&udf54;&udf53;vu10&udf54;&udf53;vz4&udf54;&udf53;vu10&udf54;to effect a transesterification reaction.
Die im vorstehenden Patentanspruch 1 definierten Verbindungen der Formel (IV) eignen sich als Zwischenprodukte zur Herstellung der Verbindungen der obigen Formel (II). Letztere können aus den erfindungsgemäßen Verbindungen dadurch erhalten werden, daß man eine erfindungsgemäße Verbindung mit einem Diazoessigsäureniederalkylester umsetzt. Das Verfahren wird zweckmäßig unter Verwendung eines Überschusses des Diens als Lösungsmittel für den Diazoessigsäureniederalkylester in Gegenwart eines Metallkatalysators, wie z. B. pulverisiertes Kupfer oder pulverisierte Kupferbronze, ausgeführt.The compounds of formula (IV) defined in the preceding claim 1 are suitable as intermediates for the preparation of the compounds of formula (II) above. The latter can be obtained from the compounds according to the invention by reacting a compound according to the invention with a lower alkyl diazoacetate. The process is conveniently carried out using an excess of the diene as solvent for the lower alkyl diazoacetate in the presence of a metal catalyst, such as powdered copper or powdered copper bronze.
Gegenstand der Erfindung sind somit halogenierte Hexa-2,4-diene gemäß Patentanspruch 1 sowie die in den Patentansprüchen 2 und 3 gekennzeichneten Verfahren zu ihrer Herstellung.The invention therefore relates to halogenated hexa-2,4-dienes according to claim 1 and to the processes for their preparation characterized in claims 2 and 3.
Die erfindungsgemäßen Verbindungen selbst können dadurch hergestellt werden, daß man ein Keton der Formel °=c:40&udf54;&udf53;vu10&udf54;&udf53;vz3&udf54; &udf53;vu10&udf54;mit dem Ylid umsetzt, das durch Dehydrohalogenierung eines 3,3-Dimethylallyl-triphenylphosphonium-halogenids erhalten worden ist.The compounds according to the invention themselves can be prepared by reacting a ketone of the formula °=c:40&udf54;&udf53;vu10&udf54;&udf53;vz3&udf54;&udf53;vu10&udf54; with the ylide which has been obtained by dehydrohalogenation of a 3,3-dimethylallyl-triphenylphosphonium halide.
Ein anderes Verfahren zur Herstellung solcher erfindungsgemäßer Verbindungen, in denen einer der Reste R¹ und R² für Trifluoromethyl und der andere für Trifluoromethyl oder Difluoromethyl steht, besteht darin, daß man eine Verbindung der Formel °=c:60&udf54;&udf53;vu10&udf54;&udf53;vz5&udf54; &udf53;vu10&udf54;durch Behandlung mit Phosphorpentoxid dehydratisiert.Another process for preparing such compounds according to the invention in which one of the radicals R¹ and R² is trifluoromethyl and the other is trifluoromethyl or difluoromethyl consists in dehydrating a compound of the formula °=c:60&udf54;&udf53;vu10&udf54;&udf53;vz5&udf54;&udf53;vu10&udf54;by treatment with phosphorus pentoxide.
Die Erfindung wird durch die folgenden Beispiele näher erläutert.The invention is explained in more detail by the following examples.
Dieses Beispiel erläutert die Herstellung von 1-Chloro-1,1-difluoro-2-chlorodifluoromethyl-5-methylhexa-2,4-dien der Formel °=c:60&udf54;&udf53;vu10&udf54;&udf53;vz5&udf54; &udf53;vu10&udf54;This example illustrates the preparation of 1-chloro-1,1-difluoro-2-chlorodifluoromethyl-5-methylhexa-2,4-diene of the formula °=c:60&udf54;&udf53;vu10&udf54;&udf53;vz5&udf54;&udf53;vu10&udf54;
Ein Gemisch aus 50,0 g 3,3-Dimethylallyl-bromid, 88,0 g Triphenylphosphin und 500 ml trockenem Toluol wurde 1 h gerührt und unter Rückfluß erhitzt und dann 18 h auf Raumtemperatur gehalten. Die weiße Ausfällung von 3,3-Dimethylallyl-triphenylphosphonium-bromid (Fp. 242°C) wurde durch Filtration gesammelt, mit Diäthyläther gewaschen und getrocknet.A mixture of 50.0 g of 3,3-dimethylallyl bromide, 88.0 g of triphenylphosphine and 500 ml of dry toluene was stirred and refluxed for 1 h and then kept at room temperature for 18 h. The white precipitate of 3,3-dimethylallyl triphenylphosphonium bromide (m.p. 242°C) was collected by filtration, washed with diethyl ether and dried.
65,0 ml einer 15%igen (G/G) Lösung von n-Butyl-lithium in Hexan wurden langsam zu einer heftig gerührten Suspension von 65,0 g 3,3-Dimethylallyl-triphenylphosphonium-bromid in 500 ml trockenem Petroläther (Kp. 30 bis 40°C) bei 0°C unter einer Stickstoffatmosphäre gegeben, worauf das Gemisch 18 h lang auf Raumtemperatur gehalten wurde. Das Gemisch wurde dann auf 0°C abgekühlt, worauf 31,44 g 1,3-Dichlorotetrafluoroaceton zugegeben wurden. Das Gemisch wurde dann während eines Zeitraums von 2 h auf Raumtempratur erwärmen gelassen, worauf die Ausfällung abfiltriert wurde. Das Filtrat wurde durch Verdampfen konzentriert, bis das Volumen ungefähr 70 ml betrug, und durch eine kurze Aluminiumoxid-Kolonne hindurchgeführt, worauf das verbliebene Lösungsmittel unter atmosphärischem Druck bei einer Temperatur von 69°C abgedampft wurde. Die zurückbleibende Flüssigkeit wurde einer fraktionierten Destillation unterworfen, und die bei 79 bis 80°C/26,6 mbar siedende Fraktion wurde gesammelt und durch IR- und NMR-Spektroskopie als 1-Chloro-1,1-difluoro-2-2chlorodifluoromethyl-5-methyl-hexa-2,4-dien- identifiziert. NMR (CCl&sub4;) ppm 1,88 bis 1,94 (m, 6H); 6,3 (d, 1H); 7,08 (d, 1H).65.0 ml of a 15% (w/w) solution of n-butyl lithium in hexane was slowly added to a vigorously stirred suspension of 65.0 g of 3,3-dimethylallyl triphenylphosphonium bromide in 500 ml of dry petroleum ether (bp 30-40°C) at 0°C under a nitrogen atmosphere and the mixture was kept at room temperature for 18 hours. The mixture was then cooled to 0°C and 31.44 g of 1,3-dichlorotetrafluoroacetone was added. The mixture was then allowed to warm to room temperature over a period of 2 hours and the precipitate was filtered off. The filtrate was concentrated by evaporation until the volume was approximately 70 ml and passed through a short alumina column and the remaining solvent was evaporated under atmospheric pressure at a temperature of 69°C. The residual liquid was subjected to fractional distillation and the fraction boiling at 79-80°C/26.6 mbar was collected and identified by IR and NMR spectroscopy as 1-chloro-1,1-difluoro-2-2chlorodifluoromethyl-5-methyl-hexa-2,4-diene. NMR (CCl₄) ppm 1.88-1.94 (m, 6H); 6.3 (d, 1H); 7.08 (d, 1H).
Analog Beispiel 1 wurden folgende Diene aus den entsprechenden Ketonen hergestellt:
- 1) 2-Methyl-5-trifluoromethylhexa-1,4-dien wurde hergestellt aus 1,1,1-Trifluoroaceton. NMR (CCl&sub4;) ppm 1,76 bis 1,82 (m, 9H); 5,85 bis 6,00 (m, 1H); 6,62 bis 6,78 (m, 1H).
- 2) 1,1-Difluoro-2-chlorodifluoromethyl-5-methylhexa-2,4-dien wurde hergestellt aus 1-Chloro-1,1,2,2-tetrafluoroaceton. IR (flüssiger Film) - 3000, 1650, 1265 cm-1.
- 3) 1,1-Difluoro-2-difluoromethyl-5-methylhexa-2,4-dien wurde hergestellt aus 1,1,3,3-Tetrafluoroaceton. NMR (CCl&sub4;) ppm 1,90 bis 2,02 (m, 6H); 5,65 bis 7,10 (m, 4H).
- 1) 2-Methyl-5-trifluoromethylhexa-1,4-diene was prepared from 1,1,1-trifluoroacetone. NMR (CCl4) ppm 1.76 to 1.82 (m, 9H); 5.85 to 6.00 (m, 1H); 6.62 to 6.78 (m, 1H).
- 2) 1,1-Difluoro-2-chlorodifluoromethyl-5-methylhexa-2,4-diene was prepared from 1-chloro-1,1,2,2-tetrafluoroacetone. IR (liquid film) - 3000, 1650, 1265 cm -1 .
- 3) 1,1-Difluoro-2-difluoromethyl-5-methylhexa-2,4-diene was prepared from 1,1,3,3-tetrafluoroacetone. NMR (CCl4) ppm 1.90 to 2.02 (m, 6H); 5.65 to 7.10 (m, 4H).
Claims (3)
WCF&sub2;-
wobei W Wasserstoff, Fluor oder Chlor ist, bedeutet und der andere Rest eine Gruppe der Formel °=c:60&udf54;&udf53;vu10&udf54;&udf53;vz5&udf54;&udf53;vu10&udf54;wobei X, Y und Z unabhängig voneinander Wasserstoff, Fluor oder Chlor sind, bedeutet. 1. Halogenated hexa-2,4-dienes of the formula IV °=c:60&udf54;&udf53;vu10&udf54;&udf53;vz5&udf54;&udf53;vu10&udf54;wherein one of the radicals R¹ and R² is a group of the formula
WCF₂-
where W is hydrogen, fluorine or chlorine and the other radical is a group of the formula °=c:60&udf54;&udf53;vu10&udf54;&udf53;vz5&udf54;&udf53;vu10&udf54;where X, Y and Z are independently hydrogen, fluorine or chlorine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB276377 | 1977-01-24 | ||
| GB3671477 | 1977-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2858263C2 true DE2858263C2 (en) | 1987-01-08 |
Family
ID=26237714
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2858264A Expired DE2858264C2 (en) | 1977-01-24 | 1978-01-24 | Intermediates for the manufacture of insecticidal halogenated esters and processes for their manufacture |
| DE2858263A Expired DE2858263C2 (en) | 1977-01-24 | 1978-01-24 | Halogenated hexa-2,4-dienes and processes for their preparation |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2858264A Expired DE2858264C2 (en) | 1977-01-24 | 1978-01-24 | Intermediates for the manufacture of insecticidal halogenated esters and processes for their manufacture |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE2858264C2 (en) |
-
1978
- 1978-01-24 DE DE2858264A patent/DE2858264C2/en not_active Expired
- 1978-01-24 DE DE2858263A patent/DE2858263C2/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2858264C2 (en) | 1986-11-20 |
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Free format text: ANDRAE, S., DIPL.-CHEM. DR.RER.NAT., 81541 MUENCHEN FLACH, D., DIPL.-PHYS., 83022 ROSENHEIM HAUG, D., DIPL.-ING. KNEISSL, R., DIPL.-CHEM. DR.RER.NAT., PAT.-ANWAELTE, 81541 MUENCHEN |