JPS5926624B2 - β−カロチンの製造方法 - Google Patents
β−カロチンの製造方法Info
- Publication number
- JPS5926624B2 JPS5926624B2 JP50040837A JP4083775A JPS5926624B2 JP S5926624 B2 JPS5926624 B2 JP S5926624B2 JP 50040837 A JP50040837 A JP 50040837A JP 4083775 A JP4083775 A JP 4083775A JP S5926624 B2 JPS5926624 B2 JP S5926624B2
- Authority
- JP
- Japan
- Prior art keywords
- solution
- carotene
- dry tetrahydrofuran
- added
- solvent
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 title claims description 21
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 title claims description 20
- 235000013734 beta-carotene Nutrition 0.000 title claims description 20
- 239000011648 beta-carotene Substances 0.000 title claims description 20
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 title claims description 18
- 229960002747 betacarotene Drugs 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000010936 titanium Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 19
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 230000002207 retinal effect Effects 0.000 claims description 13
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 claims description 2
- 150000001746 carotenes Chemical class 0.000 claims description 2
- 235000005473 carotenes Nutrition 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- -1 phosphonium halide Chemical class 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- 239000012280 lithium aluminium hydride Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 235000020945 retinal Nutrition 0.000 description 13
- 239000011604 retinal Substances 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 11
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 11
- 239000012298 atmosphere Substances 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- VQOAQMIKPYNCMV-FMQUCBEESA-N Diethylstilbestrol dimethyl ether Chemical compound C=1C=C(OC)C=CC=1C(/CC)=C(\CC)C1=CC=C(OC)C=C1 VQOAQMIKPYNCMV-FMQUCBEESA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229910010062 TiCl3 Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- IYKFYARMMIESOX-SPJNRGJMSA-N adamantanone Chemical compound C([C@H](C1)C2)[C@H]3C[C@@H]1C(=O)[C@@H]2C3 IYKFYARMMIESOX-SPJNRGJMSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- JPWJQIKXWASNOD-UHFFFAOYSA-N cycloheptylidenecycloheptane Chemical compound C1CCCCCC1=C1CCCCCC1 JPWJQIKXWASNOD-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- ZJVAWPKTWVFKHG-UHFFFAOYSA-N p-Methoxypropiophenone Chemical compound CCC(=O)C1=CC=C(OC)C=C1 ZJVAWPKTWVFKHG-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 2
- CAWFCZIEFIQKRV-UHFFFAOYSA-N 1,1'-(E)-ethene-1,2-diylbis(4-methoxybenzene) Natural products C1=CC(OC)=CC=C1C=CC1=CC=C(OC)C=C1 CAWFCZIEFIQKRV-UHFFFAOYSA-N 0.000 description 1
- KRDXURLKZNAXAQ-UHFFFAOYSA-N 2-(2-adamantylidene)adamantane Chemical compound C1C(CC2C3)CC3CC1C2=C1C(C2)CC3CC1CC2C3 KRDXURLKZNAXAQ-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- NCYCYZXNIZJOKI-OVSJKPMPSA-N Retinaldehyde Chemical compound O=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 description 1
- 229910010068 TiCl2 Inorganic materials 0.000 description 1
- SDZXPLWDXXFPSS-UKLSCZHBSA-N [Mg].CC1(C)CCCC(C)=C1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C Chemical compound [Mg].CC1(C)CCCC(C)=C1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SDZXPLWDXXFPSS-UKLSCZHBSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001579 beta-carotenes Chemical class 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- WRZSQZFOUWWQSM-UHFFFAOYSA-N cyclododecylidenecyclododecane Chemical compound C1CCCCCCCCCCC1=C1CCCCCCCCCCC1 WRZSQZFOUWWQSM-UHFFFAOYSA-N 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- HIFKCJJEFKTISP-UHFFFAOYSA-K diphenylmethanone titanium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Ti+3].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 HIFKCJJEFKTISP-UHFFFAOYSA-K 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006578 reductive coupling reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/2072—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by condensation
- C07C1/2074—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by condensation of only one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45806574A | 1974-04-05 | 1974-04-05 | |
| US458065 | 1974-04-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS516904A JPS516904A (https=) | 1976-01-20 |
| JPS5926624B2 true JPS5926624B2 (ja) | 1984-06-29 |
Family
ID=23819212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50040837A Expired JPS5926624B2 (ja) | 1974-04-05 | 1975-04-05 | β−カロチンの製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5926624B2 (https=) |
| DE (1) | DE2515011C2 (https=) |
| FR (1) | FR2266676B1 (https=) |
| GB (1) | GB1510211A (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6185226U (https=) * | 1984-11-08 | 1986-06-04 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9703992D0 (en) * | 1997-02-26 | 1997-04-16 | Rolabo Sl | Process |
-
1975
- 1975-04-04 FR FR7510675A patent/FR2266676B1/fr not_active Expired
- 1975-04-04 GB GB13972/75A patent/GB1510211A/en not_active Expired
- 1975-04-05 JP JP50040837A patent/JPS5926624B2/ja not_active Expired
- 1975-04-05 DE DE2515011A patent/DE2515011C2/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6185226U (https=) * | 1984-11-08 | 1986-06-04 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2515011C2 (de) | 1985-05-15 |
| FR2266676A1 (https=) | 1975-10-31 |
| GB1510211A (en) | 1978-05-10 |
| JPS516904A (https=) | 1976-01-20 |
| FR2266676B1 (https=) | 1980-04-04 |
| DE2515011A1 (de) | 1976-02-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Drouin et al. | Cyclization of acetylenic carbonyl compounds via their silyl enol ether derivatives: a new intramolecular C-vinylation induced by mercury (II) salts. Stereochemistry and functionalization of the intermediate vinylmercurial | |
| JP3568219B2 (ja) | 19−ノルビタミンd化合物の調製 | |
| JPH0285240A (ja) | オキシムの接触製造法 | |
| JPH10167994A (ja) | 炭素クラスター誘導体 | |
| Ohloff et al. | Synthesis of Potential Ambra Odorants: 5, 5, 9‐trimethyldecalyl derivatives | |
| JPH04288029A (ja) | パラフィン系化合物の酸化法 | |
| Luzzio et al. | Ultrasound in oxochromium (VI)-mediated transformations. 2. Ultrasound-mediated preparation and applications of chromyl chloride | |
| US4225734A (en) | Process for producing symmetrical olefins | |
| Halterman et al. | Synthesis of camphor-derived chiral cyclopentadienes via the Nazarov cyclization: Preparation of chiral bis (cyclopentadienyl) zirconium and-titanium dichlorides | |
| JPS5926624B2 (ja) | β−カロチンの製造方法 | |
| EP0168175B1 (en) | Preparation of tamoxifen | |
| Ma̧kosza et al. | Convenient preparation of metals deposited on solid supports and their use in organic synthesis | |
| Shapiro et al. | Mixture of mechanisms in the reaction of tosylhydrazones with alkyllithium reagents | |
| JPS6051450B2 (ja) | 対称オレフインの製造方法 | |
| JP2885386B2 (ja) | 金属塩錯体 | |
| EP1963339B1 (en) | Process for recycling cyclopentdienyl derivatives and preapring metallocenes from recycle, substituted cyclopentdienyl derivatives | |
| JP4418048B2 (ja) | 13−シス−レチノイン酸の製造方法 | |
| CA1292471C (en) | Preparation of piperidinylcyclopentylheptenoic acid derivatives | |
| CN110746283A (zh) | 一种β-突厥酮的合成工艺 | |
| Hoshi et al. | The synthesis of Se-alkyl alkaneselenoates via (1-iodo-1-alkenyl) dialkylboranes. | |
| Moloney et al. | The α-vinylation of β-dicarbonyl compounds by alk-1-enyl-lead triacetates | |
| PL92979B1 (https=) | ||
| Keck et al. | Intramolecular allylstannane-carbonyl condensations. Formation of vinylcyclopropane derivatives and an unusual dimeric product | |
| JP3221607B2 (ja) | 置換フェニル化合物の合成方法 | |
| JPH0112750B2 (https=) |