CH626348A5 - - Google Patents

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Publication number: CH626348A5
Authority: CH; Switzerland
Prior art keywords: formula; alkyl; mol; atoms; compound
Prior art date: 1977-07-19

Application number

CH891377A

Other languages

German (de)

English (en)

Inventor

Dieter Dr Reinehr

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.)

1977-07-19

Filing date

1977-07-19

Publication date

1981-11-13

1977-07-19 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1977-07-19 Priority to CH891377A priority Critical patent/CH626348A5/de

1978-07-10 Priority to US05/923,437 priority patent/US4213901A/en

1978-07-17 Priority to DE19782831353 priority patent/DE2831353A1/de

1978-07-18 Priority to FR7821231A priority patent/FR2398062A1/fr

1978-07-18 Priority to GB787830268A priority patent/GB2001314B/en

1978-07-19 Priority to JP8821778A priority patent/JPS5422387A/ja

1981-11-13 Publication of CH626348A5 publication Critical patent/CH626348A5/de

Links

125000000217 alkyl group Chemical group 0.000 claims description 44
125000004432 carbon atom Chemical group C* 0.000 claims description 37
238000006243 chemical reaction Methods 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 26
238000000034 method Methods 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 15
150000002816 nickel compounds Chemical class 0.000 claims description 14
-1 aryl phosphine Chemical compound 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 10
239000002879 Lewis base Substances 0.000 claims description 9
150000007527 lewis bases Chemical class 0.000 claims description 9
150000001336 alkenes Chemical class 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
WGDRAVMHLDKGGA-UHFFFAOYSA-N prop-2-en-1-imine Chemical compound [CH2]C=C[NH] WGDRAVMHLDKGGA-UHFFFAOYSA-N 0.000 claims description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
SHWZFQPXYGHRKT-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;nickel Chemical compound [Ni].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O SHWZFQPXYGHRKT-FDGPNNRMSA-N 0.000 claims 1
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
238000001228 spectrum Methods 0.000 description 10
239000007788 liquid Substances 0.000 description 9
238000004821 distillation Methods 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 8
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
ZQWDMEAJJWPULF-UHFFFAOYSA-N n-(2-methylprop-1-enyl)propan-1-imine Chemical compound CCC=NC=C(C)C ZQWDMEAJJWPULF-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
SXIFNAOBIAIYJO-SXVCMZJPSA-N (1E,3E,7E)-cyclododeca-1,3,7-triene Chemical compound C/1=C\CCCC\C=C\C=C\CC\1 SXIFNAOBIAIYJO-SXVCMZJPSA-N 0.000 description 4
SZZBPBSVMSEAIF-UHFFFAOYSA-N 2,2-dimethyl-n-prop-1-enylpropan-1-imine Chemical compound CC=CN=CC(C)(C)C SZZBPBSVMSEAIF-UHFFFAOYSA-N 0.000 description 4
SXSKAWDSYGQTAC-UHFFFAOYSA-N 2-methyl-n-(2-methylprop-1-enyl)propan-1-imine Chemical compound CC(C)C=NC=C(C)C SXSKAWDSYGQTAC-UHFFFAOYSA-N 0.000 description 4
241000233866 Fungi Species 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000012634 fragment Substances 0.000 description 4
LMYDFMYEKVBPJI-UHFFFAOYSA-N n-but-1-enylcyclohexanimine Chemical compound CCC=CN=C1CCCCC1 LMYDFMYEKVBPJI-UHFFFAOYSA-N 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000000243 solution Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
BUAVBORLHRCLMY-UHFFFAOYSA-N 11,11-dimethyl-2-propan-2-yl-1-azacyclododeca-4,8,12-triene Chemical compound CC(C)C1CC=CCCC=CCC(C)(C)C=N1 BUAVBORLHRCLMY-UHFFFAOYSA-N 0.000 description 2
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
CWCXAMOCZPXDPA-UHFFFAOYSA-N 2-ethyl-11,11-dimethyl-1-azacyclododeca-4,8,12-triene Chemical compound CCC1CC=CCCC=CCC(C)(C)C=N1 CWCXAMOCZPXDPA-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
229910052733 gallium Inorganic materials 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
AIWCPWNEDNCBBH-UHFFFAOYSA-N n,2-diethyl-3-propylnona-1,3-dien-1-amine Chemical compound CCCCCC=C(CCC)C(CC)=CNCC AIWCPWNEDNCBBH-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 2
JMWUYEFBFUCSAK-UHFFFAOYSA-L nickel(2+);octadecanoate Chemical compound [Ni+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JMWUYEFBFUCSAK-UHFFFAOYSA-L 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
230000003032 phytopathogenic effect Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
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
NVBQNJRDQVNNTR-UHFFFAOYSA-N 1,1'-biphenyl diphenyl hydrogen phosphite Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OP(O)OC1=CC=CC=C1 NVBQNJRDQVNNTR-UHFFFAOYSA-N 0.000 description 1
BRTNWPWZQXHESZ-UHFFFAOYSA-N 1,1'-biphenyl;phosphorous acid Chemical compound OP(O)O.C1=CC=CC=C1C1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1 BRTNWPWZQXHESZ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FYEYWYJOTPZYON-UHFFFAOYSA-N 1-azacyclododeca-4,8,12-triene Chemical class C1CC=CCCN=CCCC=C1 FYEYWYJOTPZYON-UHFFFAOYSA-N 0.000 description 1
XNDNXUAHCWENDU-UHFFFAOYSA-N 11-butyl-11-ethyl-2-heptan-3-yl-1-azacyclododeca-4,8,12-triene Chemical compound CCCCC(CC)C1CC=CCCC=CCC(CC)(CCCC)C=N1 XNDNXUAHCWENDU-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
YWZMGNJEPPNIGQ-UHFFFAOYSA-N 2-methyl-n-(2-methylpent-1-enyl)pentan-1-imine Chemical compound CCCC(C)C=NC=C(C)CCC YWZMGNJEPPNIGQ-UHFFFAOYSA-N 0.000 description 1
NYTPAANIMXKHJA-UHFFFAOYSA-N 2-methylprop-1-en-1-amine Chemical compound CC(C)=CN NYTPAANIMXKHJA-UHFFFAOYSA-N 0.000 description 1
GEFVPDFSQMKNLQ-UHFFFAOYSA-N 2-tert-butyl-11-methyl-1-azacyclododeca-4,8,12-triene Chemical compound CC1CC=CCCC=CCC(C(C)(C)C)N=C1 GEFVPDFSQMKNLQ-UHFFFAOYSA-N 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
241001157813 Cercospora Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
241000233654 Oomycetes Species 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
241000233614 Phytophthora Species 0.000 description 1
241000233626 Plasmopara Species 0.000 description 1
241000221300 Puccinia Species 0.000 description 1
241000221535 Pucciniales Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
HMBUSXBQVCRJSS-UHFFFAOYSA-N [Ni].C=1C=CC=CC=1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Ni].C=1C=CC=CC=1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HMBUSXBQVCRJSS-UHFFFAOYSA-N 0.000 description 1
MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals 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
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
KZLUHGRPVSRSHI-UHFFFAOYSA-N dimethylmagnesium Chemical compound C[Mg]C KZLUHGRPVSRSHI-UHFFFAOYSA-N 0.000 description 1
238000005868 electrolysis reaction Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
UOSRPRKMNSUNQQ-UHFFFAOYSA-N n-prop-1-enylpropan-2-imine Chemical compound CC=CN=C(C)C UOSRPRKMNSUNQQ-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940078494 nickel acetate Drugs 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
UNMGLSGVXHBBPH-BVHINDLDSA-L nickel(2+) (NE)-N-[(3E)-3-oxidoiminobutan-2-ylidene]hydroxylamine Chemical compound [Ni++].C\C(=N/O)\C(\C)=N\[O-].C\C(=N/O)\C(\C)=N\[O-] UNMGLSGVXHBBPH-BVHINDLDSA-L 0.000 description 1
GAIQJSWQJOZOMI-UHFFFAOYSA-L nickel(2+);dibenzoate Chemical compound [Ni+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAIQJSWQJOZOMI-UHFFFAOYSA-L 0.000 description 1
NLEUXPOVZGDKJI-UHFFFAOYSA-N nickel(2+);dicyanide Chemical compound [Ni+2].N#[C-].N#[C-] NLEUXPOVZGDKJI-UHFFFAOYSA-N 0.000 description 1
HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
DOLZKNFSRCEOFV-UHFFFAOYSA-L nickel(2+);oxalate Chemical compound [Ni+2].[O-]C(=O)C([O-])=O DOLZKNFSRCEOFV-UHFFFAOYSA-L 0.000 description 1
229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical compound CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000005672 tetraenes Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
WWVNWQJKWKSDQM-UHFFFAOYSA-N triethylarsane Chemical compound CC[As](CC)CC WWVNWQJKWKSDQM-UHFFFAOYSA-N 0.000 description 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH891377A 1977-07-19 1977-07-19 CH626348A5 (fr)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH891377A CH626348A5 (fr)	1977-07-19	1977-07-19
US05/923,437 US4213901A (en)	1977-07-19	1978-07-10	1-Aza-1,5,9-cyclododecatrienes
DE19782831353 DE2831353A1 (de)	1977-07-19	1978-07-17	1-aza-1,5,9-cyclododecatriene
FR7821231A FR2398062A1 (fr)	1977-07-19	1978-07-18	Aza-1 cyclododecatrienes-1,5,9 utilisables pour la preparation de matieres actives de produits phytosanitaires
GB787830268A GB2001314B (en)	1977-07-19	1978-07-18	1-aza-1,5,9-cyclododecatrienes
JP8821778A JPS5422387A (en)	1977-07-19	1978-07-19	11azaa1599cyclododecatriene and method for its preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH891377A CH626348A5 (fr)	1977-07-19	1977-07-19

Publications (1)

Publication Number	Publication Date
CH626348A5 true CH626348A5 (fr)	1981-11-13

Family

ID=4346203

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH891377A CH626348A5 (fr)	1977-07-19	1977-07-19

Country Status (6)

Country	Link
US (1)	US4213901A (fr)
JP (1)	JPS5422387A (fr)
CH (1)	CH626348A5 (fr)
DE (1)	DE2831353A1 (fr)
FR (1)	FR2398062A1 (fr)
GB (1)	GB2001314B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4506099A (en) *	1981-10-12	1985-03-19	Ciba-Geigy Corporation	Process for producing substituted 1,11-diaminoundecanes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH570389A5 (fr) *	1972-06-16	1975-12-15	Ciba Geigy Ag

1977
- 1977-07-19 CH CH891377A patent/CH626348A5/de not_active IP Right Cessation
1978
- 1978-07-10 US US05/923,437 patent/US4213901A/en not_active Expired - Lifetime
- 1978-07-17 DE DE19782831353 patent/DE2831353A1/de active Granted
- 1978-07-18 GB GB787830268A patent/GB2001314B/en not_active Expired
- 1978-07-18 FR FR7821231A patent/FR2398062A1/fr active Granted
- 1978-07-19 JP JP8821778A patent/JPS5422387A/ja active Granted

Also Published As

Publication number	Publication date
FR2398062B1 (fr)	1982-01-29
DE2831353A1 (de)	1979-02-08
US4213901A (en)	1980-07-22
GB2001314B (en)	1982-03-24
DE2831353C2 (fr)	1990-02-08
JPS5422387A (en)	1979-02-20
JPH0130824B2 (fr)	1989-06-22
GB2001314A (en)	1979-01-31
FR2398062A1 (fr)	1979-02-16

Publication	Publication Date	Title
DE2405856A1 (de)	1974-08-29	Katalytische dimerisierung von konjugierten dienen und katalysator dafuer
DE2330087C3 (de)	1981-02-05	Verfahren zur Herstellung von 1,2-Diazacyclododecatrienen-(1,5,9) oder l^-Diazacyclododecaenen-d)
CA1042469A (fr)	1978-11-14	Methode de production d'alcools
DE2833538A1 (de)	1980-02-14	Verfahren zur herstellung von aldehyden
DE69709159T2 (de)	2002-07-25	Kreuz-dimierisierung von olefinen
DE1668326A1 (de)	1971-08-05	Verfahren zur Herstellung eines Butadiendimeren
CH626348A5 (fr)	1981-11-13
DE1248050B (de)	1967-08-24	Verfahren zur Herstellung von Alken-(1)-yloxyorganosilanen und -siloxanen
EP0015541B1 (fr)	1984-03-07	Procédé de préparation de composés d'organolithium et d'hydrure de lithium; catalyseurs
DE2101391A1 (de)	1971-07-22	Verfahren zur Herstellung von Athylenpolymerisaten
DE2507007C2 (de)	1983-11-03	Verfahren zur Herstellung von ungesättigten Nonylaminen
DE2063038B2 (de)	1973-04-19	Verfahren zur herstellung von isoprenoligomeren
DE2154370C3 (de)	1982-05-06	Verfahren zur Herstellung von Äthern des 2,6-Dimethyl-2,7-octadien-1-ols und einige dieser Äther
DE69401599T2 (de)	1997-07-24	Verfahren zur Telomerisation von konjugierten Alkadienen
DE1810185B2 (de)	1974-05-30	Nickel (0)-katalysatoren, Verfahren zu deren Herstellung und deren Verwendung zur Oligomerisation von Butadien
DE2831385C2 (fr)	1988-01-14
DE2350197C2 (de)	1982-12-09	Verfahren zur Herstellung eines Sesquiterpens
DE2350195C2 (de)	1984-09-06	Verfahren zur Herstellung von Derivaten dimerisierter konjugierter Diene
EP0212708B1 (fr)	1990-03-14	Procédé pour l'hydroboruration d'alkènes et d'alkynes
DE2447170C2 (de)	1983-02-24	Substituierte Cyclopentene und Verfahren zu ihrer Herstellung
DE4205115C1 (fr)	1993-08-26
DE1297608B (de)	1969-06-19	Verfahren zur Herstellung von Nickel-(o)-organophosphitkomplex-verbindungen
CA1078832A (fr)	1980-06-03	1-aza-1,5,9-cyclododecatrienes
DE2350213A1 (de)	1975-04-10	Verfahren zur herstellung von trienalkoholen
DE2660599C2 (de)	1983-10-06	Allylalkohol

Legal Events

Date	Code	Title	Description
1994-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased