JPH0244477B2 - - Google Patents
Info
- Publication number
- JPH0244477B2 JPH0244477B2 JP60046852A JP4685285A JPH0244477B2 JP H0244477 B2 JPH0244477 B2 JP H0244477B2 JP 60046852 A JP60046852 A JP 60046852A JP 4685285 A JP4685285 A JP 4685285A JP H0244477 B2 JPH0244477 B2 JP H0244477B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- butadienyl
- bis
- substituted
- tetrahydrofuran
- 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 - Lifetime
Links
- -1 Bis-substituted-1,3-butadienyl Chemical class 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 239000007818 Grignard reagent Substances 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 3
- YEMJITXWLIHJHJ-UHFFFAOYSA-N di(propan-2-yloxy)silane Chemical compound CC(C)O[SiH2]OC(C)C YEMJITXWLIHJHJ-UHFFFAOYSA-N 0.000 description 3
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 3
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- TVCSNURGFFKSMT-PLNGDYQASA-N (3z)-3-chloropenta-1,3-diene Chemical compound C\C=C(/Cl)C=C TVCSNURGFFKSMT-PLNGDYQASA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- GEZFAYOYZLUQKV-UHFFFAOYSA-N 2-chloropenta-1,3-diene Chemical compound CC=CC(Cl)=C GEZFAYOYZLUQKV-UHFFFAOYSA-N 0.000 description 1
- LPVGQENACREGMI-UHFFFAOYSA-N 3-bromopenta-1,3-diene Chemical compound CC=C(Br)C=C LPVGQENACREGMI-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WMEDGFZGMIVJDS-UHFFFAOYSA-N bromo(tributoxy)silane Chemical compound CCCCO[Si](Br)(OCCCC)OCCCC WMEDGFZGMIVJDS-UHFFFAOYSA-N 0.000 description 1
- HVNLGTJPHUIWEO-UHFFFAOYSA-N buta-1,3-dien-2-yl(triethyl)silane Chemical compound CC[Si](CC)(CC)C(=C)C=C HVNLGTJPHUIWEO-UHFFFAOYSA-N 0.000 description 1
- CAFZSUDDCQOQTK-UHFFFAOYSA-N buta-1,3-dien-2-ylsilane Chemical class [SiH3]C(=C)C=C CAFZSUDDCQOQTK-UHFFFAOYSA-N 0.000 description 1
- CBVJWBYNOWIOFJ-UHFFFAOYSA-N chloro(trimethoxy)silane Chemical compound CO[Si](Cl)(OC)OC CBVJWBYNOWIOFJ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QEHKWLKYFXJVLL-UHFFFAOYSA-N dichloro(dimethoxy)silane Chemical compound CO[Si](Cl)(Cl)OC QEHKWLKYFXJVLL-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- CJVVFJRQRAQOLT-UHFFFAOYSA-N tribromo(butoxy)silane Chemical compound CCCCO[Si](Br)(Br)Br CJVVFJRQRAQOLT-UHFFFAOYSA-N 0.000 description 1
- IORQPMCLCHBYMP-UHFFFAOYSA-N trichloro(methoxy)silane Chemical compound CO[Si](Cl)(Cl)Cl IORQPMCLCHBYMP-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60046852A JPS61205286A (ja) | 1985-03-09 | 1985-03-09 | ビス―置換―１，３―ブタジエニル誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60046852A JPS61205286A (ja) | 1985-03-09 | 1985-03-09 | ビス―置換―１，３―ブタジエニル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61205286A JPS61205286A (ja) | 1986-09-11 |
| JPH0244477B2 true JPH0244477B2 (enrdf_load_stackoverflow) | 1990-10-04 |
Family
ID=12758870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60046852A Granted JPS61205286A (ja) | 1985-03-09 | 1985-03-09 | ビス―置換―１，３―ブタジエニル誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61205286A (enrdf_load_stackoverflow) |
-
1985
- 1985-03-09 JP JP60046852A patent/JPS61205286A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| ARM.KHIM.ZH=1982 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61205286A (ja) | 1986-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2567430B2 (ja) | カルビノール誘導体及びその製造方法 | |
| JP4463883B2 (ja) | １−置換−３−ヒドロキシメチル−４−（４−フルオロフェニル）テトラヒドロピリジンの化学的還元方法 | |
| JPH0244477B2 (enrdf_load_stackoverflow) | ||
| JP4599169B2 (ja) | シクロオルガニルホスファンおよびジ（アルカリ金属／アルカリ土類金属）オリゴホスファンジイドの合成方法 | |
| JP2711770B2 (ja) | エーテルを含まない有機金属アミド組成物 | |
| JPS6218484B2 (enrdf_load_stackoverflow) | ||
| JPS6222790A (ja) | 第３級炭化水素シリル化合物の製造方法 | |
| JP2001039979A (ja) | オクタヒドロピロロ［３，４−ｂ］ピリジンの製造方法 | |
| US4665209A (en) | Process for the preparation of hydrogenosilanes or halogenosilanes | |
| JP3671281B2 (ja) | トリメチルシリルアジドの製造方法 | |
| JP3137439B2 (ja) | １−アザ−２−シラシクロブタン化合物及びその製造法 | |
| JP3046258B2 (ja) | １−クロロカルボニル−４−ピペリジノピペリジンまたはその塩酸塩の製造方法 | |
| JPH0112756B2 (enrdf_load_stackoverflow) | ||
| JP2538447B2 (ja) | Ｎ−ｔｅｒｔ−ブチルジアルキルシリルマレイミドの製造方法 | |
| JP4040707B2 (ja) | ベンジル金属化合物の製造方法 | |
| JP3708131B2 (ja) | ホウ酸テトラキス（ペンタフルオロフェニル）の製造方法 | |
| JP2864985B2 (ja) | トリ（第２級アルキル）シラン化合物の製造方法 | |
| JPS603071B2 (ja) | １−（α−アシロキシアルキル）−５−フルオロウラシル類の製造方法 | |
| JPS63313792A (ja) | シリル化ケテンアセタールの製造方法 | |
| JP3650156B2 (ja) | トリアルキルシリルトリアルキルシロキシメチレン化合物の製造方法 | |
| WO1997045433A1 (fr) | Procede de preparation de composes benzyl-metal et procede de preparation de 4-phenyl-1-butenes a l'aide de ces composes | |
| JPH0465836B2 (enrdf_load_stackoverflow) | ||
| JPS60237092A (ja) | 第３級炭化水素シリル化合物の製造方法 | |
| JPS61171458A (ja) | アミン化合物の製造方法 | |
| JPH0112757B2 (enrdf_load_stackoverflow) |