SU940644A3 - Способ получени цис- и транс-изомеров замещенных дигалоидвинилциклопропанкарбоновых кислот или их эфиров - Google Patents
Способ получени цис- и транс-изомеров замещенных дигалоидвинилциклопропанкарбоновых кислот или их эфиров Download PDFInfo
- Publication number
- SU940644A3 SU940644A3 SU762322217A SU2322217A SU940644A3 SU 940644 A3 SU940644 A3 SU 940644A3 SU 762322217 A SU762322217 A SU 762322217A SU 2322217 A SU2322217 A SU 2322217A SU 940644 A3 SU940644 A3 SU 940644A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mmol
- dimethyl
- cis
- trans
- mixture
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 150000002148 esters Chemical class 0.000 title claims description 6
- 150000007513 acids Chemical class 0.000 title claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 5
- 229910052727 yttrium Inorganic materials 0.000 claims abstract 3
- 230000003647 oxidation Effects 0.000 claims abstract 2
- 238000007254 oxidation reaction Methods 0.000 claims abstract 2
- -1 hydroxide alkali metal Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005695 dehalogenation reaction Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 27
- 239000000203 mixture Substances 0.000 claims 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 14
- 239000010410 layer Substances 0.000 claims 13
- 239000000243 solution Substances 0.000 claims 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 12
- 239000007864 aqueous solution Substances 0.000 claims 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 8
- 239000000460 chlorine Chemical group 0.000 claims 6
- 238000004821 distillation Methods 0.000 claims 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 6
- 238000010992 reflux Methods 0.000 claims 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims 5
- 238000005481 NMR spectroscopy Methods 0.000 claims 5
- 238000002329 infrared spectrum Methods 0.000 claims 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- NZWWZHKTQANWRM-UHFFFAOYSA-N 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropane-1-carboxylic acid Chemical compound CC1(C)C(CC(Cl)(Cl)Cl)C1C(O)=O NZWWZHKTQANWRM-UHFFFAOYSA-N 0.000 claims 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 3
- 229910052770 Uranium Inorganic materials 0.000 claims 3
- 238000004458 analytical method Methods 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 239000007789 gas Substances 0.000 claims 3
- 238000004817 gas chromatography Methods 0.000 claims 3
- 150000004702 methyl esters Chemical class 0.000 claims 3
- DCOMZKOIMVSQLU-UHFFFAOYSA-N 1-[2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropyl]ethanone Chemical compound CC(=O)C1C(CC(Cl)(Cl)Cl)C1(C)C DCOMZKOIMVSQLU-UHFFFAOYSA-N 0.000 claims 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 2
- 102100025698 Cytosolic carboxypeptidase 4 Human genes 0.000 claims 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 101000932590 Homo sapiens Cytosolic carboxypeptidase 4 Proteins 0.000 claims 2
- 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 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 2
- 101001033003 Mus musculus Granzyme F Proteins 0.000 claims 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 2
- 239000005708 Sodium hypochlorite Substances 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 239000003518 caustics Substances 0.000 claims 2
- 238000004587 chromatography analysis Methods 0.000 claims 2
- 239000012230 colorless oil Substances 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 2
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- 239000003921 oil Substances 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims 2
- HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 claims 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 1
- NJAYZISKWWQCJX-UHFFFAOYSA-N 2-methylhept-6-en-3-one Chemical compound CC(C)C(=O)CCC=C NJAYZISKWWQCJX-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 102100022311 SPRY domain-containing SOCS box protein 4 Human genes 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- 101150069080 Spsb4 gene Proteins 0.000 claims 1
- 101100366687 Streptococcus agalactiae serotype V (strain ATCC BAA-611 / 2603 V/R) ssb4 gene Proteins 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000013256 coordination polymer Substances 0.000 claims 1
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000003999 initiator Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- YCUDCHKDRGFXPX-UHFFFAOYSA-N methyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropane-1-carboxylate Chemical compound COC(=O)C1C(CC(Cl)(Cl)Cl)C1(C)C YCUDCHKDRGFXPX-UHFFFAOYSA-N 0.000 claims 1
- PKAHQJNJPDVTDP-UHFFFAOYSA-N methyl cyclopropanecarboxylate Chemical compound COC(=O)C1CC1 PKAHQJNJPDVTDP-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000012047 saturated solution Substances 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 235000010265 sodium sulphite Nutrition 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000005283 haloketone group Chemical group 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- 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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50018296A JPS5195010A (en) | 1975-02-12 | 1975-02-12 | Arukiru 3*5*5*55 tetoraharogenopenchiruketonjudotainoseizohoho |
| JP50018298A JPS6059221B2 (ja) | 1975-02-12 | 1975-02-12 | アルキルシクロプロピルケトン誘導体の製造方法 |
| JP50018295A JPS5195043A (en) | 1975-02-12 | 1975-02-12 | beeta jiharogenoetenirushikuropuropanjudotaino seizohoho |
| JP1829775A JPS5721173B2 (enExample) | 1975-02-12 | 1975-02-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU940644A3 true SU940644A3 (ru) | 1982-06-30 |
Family
ID=27456930
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762322217A SU940644A3 (ru) | 1975-02-12 | 1976-02-11 | Способ получени цис- и транс-изомеров замещенных дигалоидвинилциклопропанкарбоновых кислот или их эфиров |
| SU782618098A SU1075972A3 (ru) | 1975-02-12 | 1978-05-29 | Способ получени производных @ -дигалоидвинилциклопропана |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782618098A SU1075972A3 (ru) | 1975-02-12 | 1978-05-29 | Способ получени производных @ -дигалоидвинилциклопропана |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4740612A (enExample) |
| CA (1) | CA1146580A (enExample) |
| CH (3) | CH628016A5 (enExample) |
| DE (1) | DE2605398C3 (enExample) |
| DK (1) | DK55376A (enExample) |
| FR (1) | FR2300755A1 (enExample) |
| GB (1) | GB1498931A (enExample) |
| IL (2) | IL48977A (enExample) |
| IT (1) | IT1053979B (enExample) |
| NL (1) | NL168214C (enExample) |
| SU (2) | SU940644A3 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4681953A (en) * | 1974-09-10 | 1987-07-21 | Sagami Chemical Research Center | Process for preparing dihalovinylcyclopropanecarboxylates |
| DE2638356A1 (de) * | 1976-08-26 | 1978-03-02 | Bayer Ag | Verfahren zur herstellung vinylsubstituierter cyclopropancarbonsaeureester |
| GB1515049A (en) * | 1976-10-22 | 1978-06-21 | Ici Ltd | Preparation of halogenated aldehydes |
| US4166064A (en) | 1978-02-13 | 1979-08-28 | Fmc Corporation | Process for preparing high cis 3-(2,2,2-trichloroethyl)-2,2-dimethylcyclopropane-1-carboxylates |
| DE2923773A1 (de) * | 1979-06-12 | 1980-12-18 | Bayer Ag | Verfahren zur herstellung von trans-3,3-dimethyl-cyclopropan-1,2-dicarbonsaeure |
| DE3201481A1 (de) * | 1982-01-20 | 1983-09-08 | Bayer Ag, 5090 Leverkusen | Halogenalkylsubstituierte cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| EP0095047B1 (de) * | 1982-05-05 | 1985-11-27 | Bayer Ag | Verfahren zur Herstellung von 3-vinylsubstituierten 2,2-Dimethylcyclopropan-1-carbonsäuren bzw. ihren Estern und neue Zwischenprodukte dafür |
| GB8419339D0 (en) * | 1984-07-30 | 1984-09-05 | Elliott M | Pesticides |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2561516A (en) * | 1948-02-20 | 1951-07-24 | Us Rubber Co | Trichloromethylalkenes |
| US2554533A (en) * | 1949-02-08 | 1951-05-29 | Us Rubber Co | Bromo-trichloro butenyl acetate |
| US3122587A (en) * | 1959-11-13 | 1964-02-25 | Union Carbide Corp | Process of producing 6-halo-2, 5-dimethylhexanone-3 |
| GB920855A (en) * | 1960-05-08 | 1963-03-13 | Aharon Katchalsky | A process for the preparation of telomers or adducts |
| BE622939A (enExample) * | 1961-09-28 | |||
| FR1356949A (fr) * | 1962-12-13 | 1964-04-03 | Rhone Poulenc Sa | Procédé de préparation de dérivés de l'acide cyclopropanecarboxylique |
| US3652652A (en) * | 1962-12-21 | 1972-03-28 | Rhone Poulenc Sa | 3-methallyllevulinates and preparation thereof |
| US3310589A (en) * | 1964-01-29 | 1967-03-21 | Grace W R & Co | Dibromodifluoromethane addition to olefines |
| US3862978A (en) * | 1967-08-24 | 1975-01-28 | Dow Chemical Co | Catalytic synthesis of organic halogen compounds from an ethylenically unsaturated compound and a halogenated organic compound |
| JPS5198248A (enExample) * | 1975-02-24 | 1976-08-30 |
-
1976
- 1976-02-02 GB GB4037/76A patent/GB1498931A/en not_active Expired
- 1976-02-03 NL NLAANVRAGE7601063,A patent/NL168214C/xx not_active IP Right Cessation
- 1976-02-05 IL IL48977A patent/IL48977A/xx unknown
- 1976-02-11 DK DK55376*#A patent/DK55376A/da not_active Application Discontinuation
- 1976-02-11 DE DE2605398A patent/DE2605398C3/de not_active Expired
- 1976-02-11 CA CA000245539A patent/CA1146580A/en not_active Expired
- 1976-02-11 IT IT48059/76A patent/IT1053979B/it active
- 1976-02-11 SU SU762322217A patent/SU940644A3/ru active
- 1976-02-11 FR FR7603734A patent/FR2300755A1/fr active Granted
- 1976-02-12 CH CH173576A patent/CH628016A5/de not_active IP Right Cessation
-
1978
- 1978-05-29 SU SU782618098A patent/SU1075972A3/ru active
-
1980
- 1980-04-02 CH CH262080A patent/CH631961A5/de not_active IP Right Cessation
- 1980-08-28 CH CH646280A patent/CH623557A5/de not_active IP Right Cessation
-
1981
- 1981-05-10 IL IL62828A patent/IL62828A0/xx unknown
-
1986
- 1986-02-05 US US06/825,966 patent/US4740612A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CH623557A5 (enExample) | 1981-06-15 |
| IL62828A0 (en) | 1981-07-31 |
| DE2605398C3 (de) | 1980-07-31 |
| IT1053979B (it) | 1981-10-10 |
| DK55376A (da) | 1976-08-13 |
| IL48977A (en) | 1983-05-15 |
| CA1146580A (en) | 1983-05-17 |
| SU1075972A3 (ru) | 1984-02-23 |
| US4740612A (en) | 1988-04-26 |
| DE2605398B2 (de) | 1979-11-15 |
| CH631961A5 (de) | 1982-09-15 |
| IL48977A0 (en) | 1976-04-30 |
| NL168214C (nl) | 1982-03-16 |
| FR2300755B1 (enExample) | 1978-11-10 |
| FR2300755A1 (fr) | 1976-09-10 |
| NL7601063A (nl) | 1976-08-16 |
| GB1498931A (en) | 1978-01-25 |
| CH628016A5 (de) | 1982-02-15 |
| DE2605398A1 (de) | 1976-08-26 |
| NL168214B (nl) | 1981-10-16 |
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