CH620417A5 - - Google Patents

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Publication number: CH620417A5
Authority: CH; Switzerland
Prior art keywords: formula; carried out; coor; catalyst; carbon atoms
Prior art date: 1976-05-25

Application number

CH639477A

Other languages

English (en)

French (fr)

Inventor

Per Dausell Klemmensen

Hans Kolind-Andersen

Hans Berg Madsen

Original Assignee

Cheminova As

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.)

1976-05-25

Filing date

1977-05-24

Publication date

1980-11-28

1977-05-24 Application filed by Cheminova As filed Critical Cheminova As

1980-11-28 Publication of CH620417A5 publication Critical patent/CH620417A5/fr

Links

ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
238000000034 method Methods 0.000 claims description 20
150000002596 lactones Chemical class 0.000 claims description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 11
239000003054 catalyst Substances 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
230000002140 halogenating effect Effects 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
230000026030 halogenation Effects 0.000 claims description 5
238000005658 halogenation reaction Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000002585 base Substances 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
230000032050 esterification Effects 0.000 claims description 4
238000005886 esterification reaction Methods 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000002841 Lewis acid Substances 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
238000005695 dehalogenation reaction Methods 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
150000007517 lewis acids Chemical class 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
125000001453 quaternary ammonium group Chemical group 0.000 claims 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
-1 aliphatic carboxylic ester Chemical class 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 7
XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical class CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 7
XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000006114 decarboxylation reaction Methods 0.000 description 3
PZNDLNJJUMSXTN-UHFFFAOYSA-N ethyl 5,5-dichloro-3-(2-chloropropan-2-yl)pent-4-enoate Chemical compound CCOC(=O)CC(C(C)(C)Cl)C=C(Cl)Cl PZNDLNJJUMSXTN-UHFFFAOYSA-N 0.000 description 3
YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
239000003586 protic polar solvent Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 description 1
MNQLVKDZYHGRNW-UHFFFAOYSA-N 2-diazoacetonitrile Chemical compound [N-]=[N+]=CC#N MNQLVKDZYHGRNW-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
GNZJQQJWLQWKNU-UHFFFAOYSA-N 5,5-dichloro-3-(2-chloropropan-2-yl)pent-4-enoic acid Chemical compound CC(C(CC(=O)O)C=C(Cl)Cl)(C)Cl GNZJQQJWLQWKNU-UHFFFAOYSA-N 0.000 description 1
IEBXZRQOXHLIGF-UHFFFAOYSA-N 5,5-dimethyl-4-(2-methylprop-1-enyl)oxolan-2-one Chemical compound CC(C)=CC1CC(=O)OC1(C)C IEBXZRQOXHLIGF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
ZQSMYJDVVLXXCI-UHFFFAOYSA-N diethyl 2-(1,1,4-trichloro-4-methylpent-1-en-3-yl)propanedioate Chemical compound CCOC(=O)C(C(C=C(Cl)Cl)C(C)(C)Cl)C(=O)OCC ZQSMYJDVVLXXCI-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
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 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
238000009434 installation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005086 pumping Methods 0.000 description 1
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
229940070846 pyrethrins Drugs 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000011282 treatment Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/20—Unsaturated compounds having a carboxyl group bound to a five-membered ring
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/04—Saturated compounds having a carboxyl group bound to a three or four-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH639477A 1976-05-25 1977-05-24 CH620417A5 (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB21630/76A GB1503857A (en)	1976-05-25	1976-05-25	Production of chrysanthemic acid esters and homologues thereof

Publications (1)

Publication Number	Publication Date
CH620417A5 true CH620417A5 (xx)	1980-11-28

Family

ID=10166166

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH639477A CH620417A5 (xx)	1976-05-25	1977-05-24

Country Status (11)

Country	Link
US (1)	US4138584A (xx)
JP (1)	JPS52144654A (xx)
BE (1)	BE855050A (xx)
CA (1)	CA1116178A (xx)
CH (1)	CH620417A5 (xx)
DE (1)	DE2723447A1 (xx)
ES (1)	ES459079A1 (xx)
FR (1)	FR2352786A1 (xx)
GB (1)	GB1503857A (xx)
IT (1)	IT1078996B (xx)
NL (1)	NL7705543A (xx)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1523816A (en) *	1976-07-19	1978-09-06	Cheminova As	Preparation of (2,2-disubstituted vinyl)-y-butyrolactione
DE2710174A1 (de) *	1977-03-09	1978-09-14	Bayer Ag	Verfahren zur herstellung von dihalogenvinyl-cyclopropancarbonsaeuren und deren ester
DE2710151A1 (de) *	1977-03-09	1978-09-14	Bayer Ag	Verfahren zur herstellung von dihalogenvinyl-gamma-butyrolactonen
DE2740849A1 (de) *	1977-09-10	1979-03-22	Bayer Ag	Verfahren zur herstellung von halogenvinylsubstituierten tetrahydrofuran-2-onen
DE2747824A1 (de) *	1977-10-26	1979-05-03	Bayer Ag	Verfahren zur herstellung von halogenvinyl-gamma-butyrolactonen
IT1200400B (it) *	1985-03-05	1989-01-18	Montedison Spa	Procedimento per la preparazione di 2-alchil ciclopent-2-enoni
DE19922934A1 (de) *	1999-05-19	2000-11-23	Bayer Ag	Neue Halogenverbindungen

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1269127A (fr) *	1960-06-20	1961-08-11	Rhone Poulenc Sa	Procédé de préparation de l'acide chrysanthémique
US3184509A (en) *	1962-07-23	1965-05-18	Lilly Co Eli	Derivatives of cyclopropanecarboxamide
US3299100A (en) *	1963-11-20	1967-01-17	Gulf Oil Corp	Manufacture of butyrolactones
US4000180A (en) *	1974-08-14	1976-12-28	Imperial Chemical Industries Limited	Process for preparing 2-dihalovinyl-3,3-dimethyl cyclo propane derivatives
GB1519290A (en) *	1974-08-14	1978-07-26	Ici Ltd	Process for preparing substituted cyclopropanes
IN142702B (xx) *	1974-09-10	1977-08-20	Sagami Chem Res
AU511487B2 (en) *	1975-05-16	1980-08-21	Imperial Chemical Industries Ltd	Cyclopropane derivatives
GB1532985A (en) *	1975-05-27	1978-11-22	Ici Ltd	Process for preparing vinyl substituted furan derivatives
GB1527989A (en) *	1975-07-11	1978-10-11	Ici Ltd	4-dihalovinyl-3,3-dimethylbutyrolactones and their use in the production of insecticides
FR2353514A1 (fr) *	1976-06-03	1977-12-30	Sumitomo Chemical Co	Procede pour la preparation de derives d'acides 2,2-dimethyl-3-(2,2-dihalogenovinyl)-cyclopropane-carboxyliques

1976
- 1976-05-25 GB GB21630/76A patent/GB1503857A/en not_active Expired
1977
- 1977-05-18 NL NL7705543A patent/NL7705543A/xx not_active Application Discontinuation
- 1977-05-23 US US05/799,587 patent/US4138584A/en not_active Expired - Lifetime
- 1977-05-24 DE DE19772723447 patent/DE2723447A1/de not_active Ceased
- 1977-05-24 ES ES459079A patent/ES459079A1/es not_active Expired
- 1977-05-24 CA CA279,261A patent/CA1116178A/en not_active Expired
- 1977-05-24 CH CH639477A patent/CH620417A5/fr not_active IP Right Cessation
- 1977-05-24 FR FR7715849A patent/FR2352786A1/fr active Granted
- 1977-05-25 BE BE177918A patent/BE855050A/xx not_active IP Right Cessation
- 1977-05-25 JP JP5998177A patent/JPS52144654A/ja active Pending
- 1977-05-25 IT IT23985/77A patent/IT1078996B/it active

Also Published As

Publication number	Publication date
IT1078996B (it)	1985-05-08
JPS52144654A (en)	1977-12-02
CA1116178A (en)	1982-01-12
ES459079A1 (es)	1978-04-16
US4138584A (en)	1979-02-06
FR2352786A1 (fr)	1977-12-23
FR2352786B1 (xx)	1983-10-07
GB1503857A (en)	1978-03-15
BE855050A (fr)	1977-09-16
DE2723447A1 (de)	1977-12-15
NL7705543A (nl)	1977-11-29

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FR2517677A1 (fr)	1983-06-10	Nouveaux ethers dont les restes organiques comportent des atomes chiraux, leur procede de preparation et leur application au dedoublement des alcools ou de certains composes de structure hemiacetalique.
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CA2626588C (fr)	2014-11-25	Nouveau procede de preparation d'hydroxy-acides gras insatures
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CH618434A5 (xx)	1980-07-31
Singh et al.	2010	A dimethylsulfonium methylide mediated highly regioselective olefination of conjugated polyolefin 1, 1-dioates to conjugated polyene-2-yl-malonates and their applications in Diels–Alder reactions
CH626319A5 (en)	1981-11-13	Process for the preparation of lower alkyl esters of racemic trans-2,2-disubstituted-1,3-cyclopropanedicarboxylic acids
EP0122202B1 (fr)	1987-06-16	Nouveaux tétra-alkyl-2,2,5,5 cyclohexanone-4 ol-1 et leurs dérivés sulfonylés, leur procédé et leurs intermédiaires de préparation et leur application à la synthèse de lactones cyclopropaniques cis
EP0021925A1 (fr)	1981-01-07	Procédé de préparation d'alcools alpha-cyanés optiquement actifs
FR2460951A1 (fr)	1981-01-30	Procede de preparation de derives de 15-hydroxyimino-e-homoeburnane et composes obtenus par ce procede
JPS6160822B2 (xx)	1986-12-23
CA1228869A (fr)	1987-11-03	Tetra-alkyl-2,2,5,5 cyclohexanone-1,4 et leur procede de preparation
CH621784A5 (xx)	1981-02-27
EP0466583B1 (fr)	1994-12-14	Procédé de préparation de la diméthyl-2,5 hydroxy-4 (2H)furanone-3
FR2499979A1 (fr)	1982-08-20	Procede d'epimerisation d'acides trans chrysanthemiques
WO1985004873A1 (fr)	1985-11-07	Composes imines de synthese contenant un atome de carbone quaternaire chiral, leur preparation et leur utilisation
EP0119899B1 (fr)	1986-03-05	Nouveau procédé de préparation de dérivés de l'acide pen-4-énoique
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JPH0415222B2 (xx)	1992-03-17
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