CH630599A5 - Process for the preparation of 2-(2',2'-dihalovinyl)- and 2-(2',2',2'-trihaloethyl)-cyclobutanones - Google Patents

Process for the preparation of 2-(2',2'-dihalovinyl)- and 2-(2',2',2'-trihaloethyl)-cyclobutanones Download PDF

Info

Publication number: CH630599A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; atoms; methyl; hydrogen
Prior art date: 1977-03-31

Application number

CH407277A

Other languages

German (de)

English (en)

Inventor

Hans Dr Greuter

Pierre Dr Martin

Daniel Dr Bellus

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1977-03-31

Filing date

1977-03-31

Publication date

1982-06-30

1977-03-31 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1977-03-31 Priority to CH407277A priority Critical patent/CH630599A5/de

1978-03-28 Priority to DE19782813336 priority patent/DE2813336A1/de

1978-03-28 Priority to SU782596900A priority patent/SU959621A3/ru

1978-03-28 Priority to FI780931A priority patent/FI780931A7/fi

1978-03-29 Priority to GR55830A priority patent/GR73133B/el

1978-03-29 Priority to CA299,989A priority patent/CA1090825A/en

1978-03-29 Priority to DD78204454A priority patent/DD136834A5/xx

1978-03-30 Priority to BE186393A priority patent/BE865482A/xx

1978-03-30 Priority to BR7801975A priority patent/BR7801975A/pt

1978-03-30 Priority to IT21803/78A priority patent/IT1094007B/it

1978-03-30 Priority to AR271609A priority patent/AR223459A1/es

1978-03-30 Priority to HU78CI1822A priority patent/HU175718B/hu

1978-03-30 Priority to FR7809242A priority patent/FR2385673A1/fr

1978-03-30 Priority to SE7803601A priority patent/SE7803601L/xx

1978-03-30 Priority to DK140678A priority patent/DK140678A/da

1978-03-30 Priority to GB12558/78A priority patent/GB1598472A/en

1978-03-30 Priority to NO781113A priority patent/NO781113L/no

1978-03-30 Priority to ZA00781809A priority patent/ZA781809B/xx

1978-03-30 Priority to ES468361A priority patent/ES468361A1/es

1978-03-30 Priority to CS782049A priority patent/CS199525B2/cs

1978-03-30 Priority to IL54393A priority patent/IL54393A/xx

1978-03-30 Priority to AT225178A priority patent/AT353771B/de

1978-03-31 Priority to MX786985U priority patent/MX5100E/es

1978-03-31 Priority to TR20096A priority patent/TR20096A/xx

1978-03-31 Priority to PL1978205740A priority patent/PL107808B1/pl

1978-03-31 Priority to AU34644/78A priority patent/AU520526B2/en

1978-03-31 Priority to NL7803466A priority patent/NL7803466A/xx

1978-03-31 Priority to JP3802078A priority patent/JPS53121741A/ja

1979-03-16 Priority to US06/021,273 priority patent/US4234517A/en

1982-06-30 Publication of CH630599A5 publication Critical patent/CH630599A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 55
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
239000001257 hydrogen Substances 0.000 claims abstract description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
239000000460 chlorine Substances 0.000 claims abstract description 11
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052794 bromium Inorganic materials 0.000 claims abstract description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 14
-1 phenylmercapto Chemical class 0.000 claims description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
150000007530 organic bases Chemical class 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 11
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
150000003254 radicals Chemical class 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
125000005270 trialkylamine group Chemical group 0.000 claims description 4
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
239000012320 chlorinating reagent Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 1
239000000575 pesticide Substances 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
239000002253 acid Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
150000002596 lactones Chemical class 0.000 description 11
239000000203 mixture Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000002140 halogenating effect Effects 0.000 description 7
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
150000001336 alkenes Chemical class 0.000 description 6
239000011230 binding agent Substances 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000002904 solvent Substances 0.000 description 5
CRJUMZUCOGGELR-UHFFFAOYSA-N 7,7-dichloro-5-hydroxy-4,4-dimethylhept-6-enoic acid Chemical compound OC(=O)CCC(C)(C)C(O)C=C(Cl)Cl CRJUMZUCOGGELR-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
OJOFMBWHEOLBOH-UHFFFAOYSA-N 5,5-dichloropent-4-enoic acid Chemical compound OC(=O)CCC=C(Cl)Cl OJOFMBWHEOLBOH-UHFFFAOYSA-N 0.000 description 3
MIMQLIOZZYBPAY-UHFFFAOYSA-N 5,5-dichloropent-4-enoyl chloride Chemical compound ClC(Cl)=CCCC(Cl)=O MIMQLIOZZYBPAY-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
244000309464 bull Species 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
239000002917 insecticide Substances 0.000 description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
MCXXMJLSPWOVAF-UHFFFAOYSA-N 2-(2,2-dichloroethenyl)-3,3-dimethylcyclobutan-1-one Chemical compound CC1(C)CC(=O)C1C=C(Cl)Cl MCXXMJLSPWOVAF-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
PNRIZWCHOZUISE-UHFFFAOYSA-N 4,4,4-trichloro-3-hydroxybutanoic acid Chemical compound ClC(Cl)(Cl)C(O)CC(O)=O PNRIZWCHOZUISE-UHFFFAOYSA-N 0.000 description 2
KWWSYWYLJHRUIV-UHFFFAOYSA-N 7,7,7-trichloro-5-hydroxy-4,4-dimethylheptanoic acid Chemical compound OC(=O)CCC(C)(C)C(O)CC(Cl)(Cl)Cl KWWSYWYLJHRUIV-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
QPTWKDNRYCGMJM-UHFFFAOYSA-N ethyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=C(Cl)Cl)C1(C)C QPTWKDNRYCGMJM-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
239000008096 xylene Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
SFPQDYSOPQHZAQ-UHFFFAOYSA-N 2-methoxypropanenitrile Chemical compound COC(C)C#N SFPQDYSOPQHZAQ-UHFFFAOYSA-N 0.000 description 1
SLOAHHQEFMJCAQ-UHFFFAOYSA-N 3,3-dimethyl-2-(2,2,2-trichloroethyl)cyclobutan-1-one Chemical compound CC1(C)CC(=O)C1CC(Cl)(Cl)Cl SLOAHHQEFMJCAQ-UHFFFAOYSA-N 0.000 description 1
KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 description 1
LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
150000004652 butanoic acids Chemical class 0.000 description 1
UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006352 cycloaddition reaction Methods 0.000 description 1
SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical class O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
235000019394 potassium persulphate Nutrition 0.000 description 1
239000000047 product Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000006004 trihaloethyl group Chemical group 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/38—Acyl halides
- C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
- C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/54—Halogenated acrylic or methacrylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/115—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH407277A 1977-03-31 1977-03-31 Process for the preparation of 2-(2',2'-dihalovinyl)- and 2-(2',2',2'-trihaloethyl)-cyclobutanones CH630599A5 (en)

Priority Applications (29)

Application Number	Priority Date	Filing Date	Title
CH407277A CH630599A5 (en)	1977-03-31	1977-03-31	Process for the preparation of 2-(2',2'-dihalovinyl)- and 2-(2',2',2'-trihaloethyl)-cyclobutanones
DE19782813336 DE2813336A1 (de)	1977-03-31	1978-03-28	2-(2',2'-dihalogenvinyl)- und 2-(2', 2',2'-trihalogenaethyl)-cyclobutanone
SU782596900A SU959621A3 (ru)	1977-03-31	1978-03-28	Способ получени производных циклобутанона
FI780931A FI780931A7 (fi)	1977-03-31	1978-03-28	2-(2'2'-dihalogenvinyl)-och 2-(2'2'2'-trihalogenetyl)-cyklobutanoner foerfarande foer deras framstaellning och deras anvaendning
GR55830A GR73133B (cs)	1977-03-31	1978-03-29
CA299,989A CA1090825A (en)	1977-03-31	1978-03-29	2-(2',2'-dihalovinyl)-cyclobutanones and 2-(2',2',2'- trihaloethyl)-cyclobutanones
DD78204454A DD136834A5 (de)	1977-03-31	1978-03-29	Verfahren zur herstellung von 2-(2',2'-dihalogenvinyl-und 2-(2',2',2'-trihalogenaethyl)-cyclobutanonen
BE186393A BE865482A (fr)	1977-03-31	1978-03-30	Halogenovinyl- et trihalogenoethyl-cyclobutanones utilisables pour la preparation de composes insecticides
BR7801975A BR7801975A (pt)	1977-03-31	1978-03-30	Composto organico,processo para sua preparacao e seu emprego
IT21803/78A IT1094007B (it)	1977-03-31	1978-03-30	2-aperta par.tonda 2',2'-di-alogenovinil chiusa par.tonda-ciclobutanoni,procedimento per la loro preparazione e loro impiego
AR271609A AR223459A1 (es)	1977-03-31	1978-03-30	2-(2',2'-dihalogenovinil)-y 2-(2',2',2'-trihalogenoetil-ciclobutanona)y procedimiento para su preparacion
HU78CI1822A HU175718B (hu)	1977-03-31	1978-03-30	Sposob poluchenija 2-/2'-dikhlorvinil/- i 2-/2',2',2'-trikhlor-ehtil/-ciklobutanonov
FR7809242A FR2385673A1 (fr)	1977-03-31	1978-03-30	Halogenovinyl- et trihalogenoethyl-cyclobutanones utilisables pour la preparation de composes insecticides
SE7803601A SE7803601L (sv)	1977-03-31	1978-03-30	Cyklobutanoner
DK140678A DK140678A (da)	1977-03-31	1978-03-30	2-(2!,2!-dihalogenvinyl)- og 2-(2!,2!-trihalogenethyl)-cyclobutanoner samt fremgangsmaade til fremstilling deraf
GB12558/78A GB1598472A (en)	1977-03-31	1978-03-30	2-(2',2'-dihalovinyl)-cyclobutanones and 2-(2',2',2'-trihaloethyl)-cyclobutanones
NO781113A NO781113L (no)	1977-03-31	1978-03-30	2-(2`,2`,2`-dihalogenvinyl)- og 2-(2`,2`,2`-trihalogenetyl)-cyklobutanon
ZA00781809A ZA781809B (en)	1977-03-31	1978-03-30	2-(2',2'-dihalovinyl)-cyclobutanones and 2-(2',2',2'-trihaloethyl)-cyclo-butanones
ES468361A ES468361A1 (es)	1977-03-31	1978-03-30	Un procedimiento para la preparacion de acidos 2-(2'-2'-di- halogenvinil)-ciclopropancarboxilicos y sus esteres.
CS782049A CS199525B2 (en)	1977-03-31	1978-03-30	Method of producing novel 2-/2',2'-dihalogenvinyl/-and 2-/2',2',2'-trihalogenethyl0 cyclobutanones
IL54393A IL54393A (en)	1977-03-31	1978-03-30	2-(2',2'-dihalovinyl)-cyclobutanones and 2-(2',2',2'-trihaloethyl)-cyclobutanones, and their production
AT225178A AT353771B (de)	1977-03-31	1978-03-30	Verfahren zur herstellung von neuen 2-(2',2'- dihalogenvinyl)-oder(2',2',2'-trihalogenaethyl)- cyclobutanonen
MX786985U MX5100E (es)	1977-03-31	1978-03-31	Procedimiento para la produccion de 2-(2',2',-dihalovinil)-ciclobutanonas y 2-(2',2',2',-trihaloetil)-ciclobutanonas
TR20096A TR20096A (tr)	1977-03-31	1978-03-31	2-(2'2'-dihalojenovinil)-ve 2(2',2',2'-trihalojenoetil)-siklomutano lar
PL1978205740A PL107808B1 (pl)	1977-03-31	1978-03-31	Sposob wytwarzania nowych 2-/2',2'-dwuchlorowcowinylo/-cyklobutanonow i 2-/2',2',2'-trojchlorowcoetylo/-cyklobutanonow
AU34644/78A AU520526B2 (en)	1977-03-31	1978-03-31	2-(2'2'-dihalovinyi)-cyclobutanones and 2-(2'2'2'-trihaloethyl-cyclobutanones
NL7803466A NL7803466A (nl)	1977-03-31	1978-03-31	Cyclobutanonverbinding en werkwijze voor het bereiden daarvan alsmede voor het bereiden van cyclopropaancarbonzuurderivaten.
JP3802078A JPS53121741A (en)	1977-03-31	1978-03-31	Derivative of cyclobutane * its preparation and method for using said compound
US06/021,273 US4234517A (en)	1977-03-31	1979-03-16	2-(2',2'-Dihalovinyl)-cyclobutanones and 2-(2',2',2'-trihaloethyl)-cyclobutanones

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH407277A CH630599A5 (en)	1977-03-31	1977-03-31	Process for the preparation of 2-(2',2'-dihalovinyl)- and 2-(2',2',2'-trihaloethyl)-cyclobutanones

Publications (1)

Publication Number	Publication Date
CH630599A5 true CH630599A5 (en)	1982-06-30

Family

ID=4269291

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH407277A CH630599A5 (en)	1977-03-31	1977-03-31	Process for the preparation of 2-(2',2'-dihalovinyl)- and 2-(2',2',2'-trihaloethyl)-cyclobutanones

Country Status (8)

Country	Link
AT (1)	AT353771B (cs)
BE (1)	BE865482A (cs)
CH (1)	CH630599A5 (cs)
CS (1)	CS199525B2 (cs)
HU (1)	HU175718B (cs)
PL (1)	PL107808B1 (cs)
SU (1)	SU959621A3 (cs)
ZA (1)	ZA781809B (cs)

1977
- 1977-03-31 CH CH407277A patent/CH630599A5/de not_active IP Right Cessation
1978
- 1978-03-28 SU SU782596900A patent/SU959621A3/ru active
- 1978-03-30 HU HU78CI1822A patent/HU175718B/hu unknown
- 1978-03-30 BE BE186393A patent/BE865482A/xx not_active IP Right Cessation
- 1978-03-30 CS CS782049A patent/CS199525B2/cs unknown
- 1978-03-30 AT AT225178A patent/AT353771B/de not_active IP Right Cessation
- 1978-03-30 ZA ZA00781809A patent/ZA781809B/xx unknown
- 1978-03-31 PL PL1978205740A patent/PL107808B1/pl unknown

Also Published As

Publication number	Publication date
PL205740A1 (pl)	1979-03-26
PL107808B1 (pl)	1980-03-31
ATA225178A (de)	1979-05-15
HU175718B (hu)	1980-10-28
ZA781809B (en)	1979-11-28
BE865482A (fr)	1978-10-02
SU959621A3 (ru)	1982-09-15
CS199525B2 (en)	1980-07-31
AT353771B (de)	1979-12-10

Legal Events

Date	Code	Title	Description
1985-11-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2858248C2 (cs)	1987-10-08
EP0001980B1 (de)	1981-05-06	Verfahren zur Herstellung von Halogenvinyl-gamma-butyrolactonen, sowie Zwischenprodukte und ihre Herstellung
EP0001089B1 (de)	1981-10-21	Verfahren zur Herstellung von halogenvinylsubstituierten Tetrahydrofuran-2-onen, bestimmte halogenvinylsubstituierte Tetrahydrofuran-2-one
US4234517A (en)	1980-11-18	2-(2',2'-Dihalovinyl)-cyclobutanones and 2-(2',2',2'-trihaloethyl)-cyclobutanones
CH630599A5 (en)	1982-06-30	Process for the preparation of 2-(2',2'-dihalovinyl)- and 2-(2',2',2'-trihaloethyl)-cyclobutanones
CH628016A5 (de)	1982-02-15	Verfahren zur herstellung von neuen alkylcyclopropylketon-derivaten und verwendung derselben.
EP0095047A1 (de)	1983-11-30	Verfahren zur Herstellung von 3-vinylsubstituierten 2,2-Dimethylcyclopropan-1-carbonsäuren bzw. ihren Estern und neue Zwischenprodukte dafür
US4322374A (en)	1982-03-30	2,4,4,4-Tetrahalobutanoic acid halide
DE69409800T2 (de)	1998-08-13	Verfahren zur herstellung von halogenierten alkoholen
EP0025935B1 (de)	1982-12-22	Verfahren zur Herstellung von 5-(2,2,2-Trihalogenethyl)-dialkyl-tetrahydrofuran-2-onen
EP0002206A1 (de)	1979-06-13	Halogenierte Buttersäurechloride, Verfahren zu deren Herstellung und ihre Verwendung als Zwischenprodukte zur Herstellung von Schädlingsbekämpfungsmitteln
EP0290903B1 (de)	1991-09-11	Beta-Fluoracyl-beta-halogenvinylalkylether
CH644093A5 (de)	1984-07-13	Verfahren zur herstellung von 2,2-dihalogenvinyl-substituierten cyclopropancarbonsaeure-estern.
EP0103749B1 (de)	1986-07-02	Dialkoxymethyl-butyrolactone, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung
EP0051791A1 (de)	1982-05-19	2,2-Dimethylcyclobutanone und Verfahren zu ihrer Herstellung
DE2731483A1 (de)	1978-01-19	Dihalovinylsubstituierte gamma-laktone
DE3045768A1 (de)	1981-06-11	2-(2',2'-dichlor-3',3',3'-trifluorpropyl)- und 2-(2',2',3'-trichlor-3',3'-difluorporpyl)-4-chlorcyclobutan-1-one
EP0025931B1 (de)	1983-03-09	Verfahren zur Herstellung von 5-(2,2,-Dihalogenvinyl)-4,4-dialkyl-tetrahydrofuran-2-onen
DE2619321C2 (de)	1984-05-17	Oxalsäurederivate, ihre Herstellung und ihre Verwendung
EP0126225B1 (de)	1986-11-26	Verfahren zur Herstellung von substituierten Trialkylsilyloxymalonsäuredinitrilen
EP0050777A2 (de)	1982-05-05	Verfahren zur Herstellung von chlorfluoralkyl-substituierten Cyclopropancarbonsäuren und deren Derivaten und Zwischenprodukte dafür
EP0041283A1 (en)	1981-12-09	Process for the preparation of dihalomethylene-lactones
DE2621833A1 (de)	1976-11-25	Herstellung organischer saeuren
DE2402457C3 (de)	1976-03-25	Verfahren zur Herstellung von m-Phenoxybenzylalkohol
DE2842601A1 (de)	1980-04-17	Verfahren zur herstellung von 2-(2',2',2'-tribromaethyl)-4-horcyclobutan-1-onen