DD273635A5 - Verfahren zur herstellung von (aryl)-(dimethyl)-(3-(4-flouro-3-aryl-oxyphenyl)propyl)silanen - Google Patents

Verfahren zur herstellung von (aryl)-(dimethyl)-(3-(4-flouro-3-aryl-oxyphenyl)propyl)silanen Download PDF

Info

Publication number: DD273635A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; ind; aryl; dimethyl; propyl
Prior art date: 1987-09-19

Application number

DD88319868A

Other languages

German (de)

English (en)

Inventor

Hans H Schubert

Original Assignee

��@��k��

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.)

1987-09-19

Filing date

1988-09-16

Publication date

1989-11-22

1988-09-16 Application filed by ��@��k�� filed Critical ��@��k��

1989-11-22 Publication of DD273635A5 publication Critical patent/DD273635A5/de

Links

150000004756 silanes Chemical class 0.000 title abstract description 6
238000004519 manufacturing process Methods 0.000 title description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical class [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 19
238000000034 method Methods 0.000 claims abstract description 18
229910052736 halogen Inorganic materials 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims description 13
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 10
239000010949 copper Substances 0.000 abstract description 10
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 8
229910052802 copper Inorganic materials 0.000 abstract description 7
239000003513 alkali Substances 0.000 abstract description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 6
229910052784 alkaline earth metal Chemical group 0.000 abstract description 5
125000003118 aryl group Chemical group 0.000 abstract description 5
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 3
150000001342 alkaline earth metals Chemical group 0.000 abstract description 3
125000003545 alkoxy group Chemical group 0.000 abstract description 3
229910000077 silane Inorganic materials 0.000 abstract description 3
125000000217 alkyl group Chemical group 0.000 abstract 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 1
229910052783 alkali metal Inorganic materials 0.000 abstract 1
150000001340 alkali metals Chemical group 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000243 solution Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
LUVULFUQRHJDGP-UHFFFAOYSA-N 2-chloro-1-fluoro-4-prop-2-enylbenzene Chemical compound FC1=CC=C(CC=C)C=C1Cl LUVULFUQRHJDGP-UHFFFAOYSA-N 0.000 description 2
FRMMZCHSBMXASM-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)propyl-(4-ethoxyphenyl)-dimethylsilane Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(Cl)=C1 FRMMZCHSBMXASM-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 2
CJTIWGBQCVYTQE-UHFFFAOYSA-N 4-bromo-2-chloro-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1Cl CJTIWGBQCVYTQE-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000004707 phenolate Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 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 description 2
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
DECGNXVVNBDTQK-UHFFFAOYSA-N (4-ethoxyphenyl)-dimethylsilane Chemical compound CCOC1=CC=C([SiH](C)C)C=C1 DECGNXVVNBDTQK-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
KOWPUNQBGWIERF-UHFFFAOYSA-N 3-bromo-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Br)=C1 KOWPUNQBGWIERF-UHFFFAOYSA-N 0.000 description 1
YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical class O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 1
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 1
-1 4-ethoxyphenyl Chemical group 0.000 description 1
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000006459 hydrosilylation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD88319868A 1987-09-19 1988-09-16 Verfahren zur herstellung von (aryl)-(dimethyl)-(3-(4-flouro-3-aryl-oxyphenyl)propyl)silanen DD273635A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873731609 DE3731609A1 (de)	1987-09-19	1987-09-19	Verfahren zur herstellung von (aryl)-(dimethyl)-(3-(4-fluoro-3-aryloxyphenyl)propyl)silanen

Publications (1)

Publication Number	Publication Date
DD273635A5 true DD273635A5 (de)	1989-11-22

Family

ID=6336424

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88319868A DD273635A5 (de)	1987-09-19	1988-09-16	Verfahren zur herstellung von (aryl)-(dimethyl)-(3-(4-flouro-3-aryl-oxyphenyl)propyl)silanen

Country Status (11)

Country	Link
US (1)	US4920212A (fr)
EP (1)	EP0308788B1 (fr)
JP (1)	JP2705949B2 (fr)
KR (1)	KR0126769B1 (fr)
CA (1)	CA1326039C (fr)
DD (1)	DD273635A5 (fr)
DE (2)	DE3731609A1 (fr)
ES (1)	ES2061583T3 (fr)
HU (1)	HU199485B (fr)
IL (1)	IL87774A (fr)
ZA (1)	ZA886875B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3815768A1 (de) *	1988-05-09	1989-11-23	Teves Gmbh Alfred	Pneumatischer bremskraftverstaerker
US5506269A (en) *	1993-12-27	1996-04-09	Mitsui Toatsu Chemicals, Inc.	Parasiticide employing pyrethroid type compounds

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2914548A (en) *	1956-12-14	1959-11-24	Ethyl Corp	Process for producing aryloxyphenyl silanes
US3013044A (en) *	1959-06-05	1961-12-12	Olin Mathieson	Bis-aryloxyphenyl-dialkylsilanes
US3637866A (en) *	1968-02-13	1972-01-25	Us Air Force	Substituted perfluoro diphenyl ethers
DE3141860A1 (de) *	1981-10-22	1983-05-05	Bayer Ag, 5090 Leverkusen	Trifluormethyl-phenoxy-phenyl-silicium-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwuchsregulatoren
EP0224024B1 (fr) *	1985-10-26	1990-06-20	Hoechst Aktiengesellschaft	Dérivés de silanes, leur procédé de préparation, agents les contenant et leur utilisation comme pesticides
US4709068A (en) *	1986-06-02	1987-11-24	Fmc Corporation	Substituted phenyltrialkylsilane insecticides

1987
- 1987-09-19 DE DE19873731609 patent/DE3731609A1/de not_active Withdrawn
1988
- 1988-09-14 ES ES88114985T patent/ES2061583T3/es not_active Expired - Lifetime
- 1988-09-14 EP EP88114985A patent/EP0308788B1/fr not_active Expired - Lifetime
- 1988-09-14 DE DE88114985T patent/DE3886153D1/de not_active Expired - Fee Related
- 1988-09-15 ZA ZA886875A patent/ZA886875B/xx unknown
- 1988-09-16 US US07/245,404 patent/US4920212A/en not_active Expired - Fee Related
- 1988-09-16 CA CA000577603A patent/CA1326039C/fr not_active Expired - Fee Related
- 1988-09-16 JP JP63230222A patent/JP2705949B2/ja not_active Expired - Lifetime
- 1988-09-16 IL IL87774A patent/IL87774A/xx not_active IP Right Cessation
- 1988-09-16 DD DD88319868A patent/DD273635A5/de not_active IP Right Cessation
- 1988-09-16 HU HU884886A patent/HU199485B/hu not_active IP Right Cessation
- 1988-09-19 KR KR1019880012072A patent/KR0126769B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE3886153D1 (de)	1994-01-20
JP2705949B2 (ja)	1998-01-28
DE3731609A1 (de)	1989-03-30
US4920212A (en)	1990-04-24
EP0308788B1 (fr)	1993-12-08
ZA886875B (en)	1989-04-26
CA1326039C (fr)	1994-01-11
ES2061583T3 (es)	1994-12-16
HU199485B (en)	1990-02-28
JPH01113396A (ja)	1989-05-02
EP0308788A2 (fr)	1989-03-29
HUT48631A (en)	1989-06-28
IL87774A0 (en)	1989-02-28
KR0126769B1 (ko)	1998-04-03
EP0308788A3 (en)	1990-08-08
KR890005129A (ko)	1989-05-11
IL87774A (en)	1992-12-01

Legal Events

Date	Code	Title	Description
1995-06-22	ENJ	Ceased due to non-payment of renewal fee

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Katritzky et al.	1996	2-bromo-3, 3, 3-trifluoropropene: A facile trifluoromethylacetylene anion synthon
DD273635A5 (de)	1989-11-22	Verfahren zur herstellung von (aryl)-(dimethyl)-(3-(4-flouro-3-aryl-oxyphenyl)propyl)silanen
DE3939535A1 (de)	1991-06-06	Verfahren zur herstellung teilfluorierter alkohole
US4473709A (en)	1984-09-25	Pyrethroid intermediates and process
DE2850502A1 (de)	1979-05-31	2,4,4,4-tetrachlorbuttersaeure-1,2,4, 4,4-pentachlor-but-1-enylester
JPS6357580A (ja)	1988-03-12	２，３−ジヒドロフラン誘導体及びその製造方法、並びにテトラヒドロフランの製造における中間生成物としての使用
DD201792A5 (de)	1983-08-10	Verfahren zur herstellung der 2,3,4,5-tetrahydro-1-benzoxepin-3,5-dion-derivate
DE69821934T2 (de)	2004-07-29	Verfahren zur herstellung von n-cyclopropylanilinen und zwischenverbindungen zu ihrer herstellung
EP0391212B1 (fr)	1994-05-25	Procédé de préparation de composés de stilbène bifonctionnels ayant la configuration Z, composés de stilbène ayant cette configuration ainsi que leur utilisation pour la préparation de polymères
DD254733A5 (de)	1988-03-09	Verfahren zur herstellung von phenoxyalkanoltriazolverbindungen
DE2219455C3 (de)	1979-02-08	Verfahren zur Herstellung von Aldehyden sowie (3,4-IsopropylidendioxyphenyD-acetaldehyd
EP0308808B1 (fr)	1991-12-18	Procédé pour la préparation d'éthers 2-fluoro-5-allyl-diphényliques
DE69118175T2 (de)	1996-10-02	Neues disulfidderivat
DE2802281A1 (de)	1978-07-27	Neue phenylen-bis-diketone, ihre herstellung und deren verwendung
DE3244641A1 (de)	1983-06-09	Verfahren zur herstellung von zwischenprodukten fuer die pyrethroid-synthese
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EP0280975B1 (fr)	1992-07-08	Procédés pour la préparation d'aldéhydes benzoiques substitués et produits intermédiaires obtenus dans ces procédés
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