GB823958A - Organomagnesium chloride complexes - Google Patents
Organomagnesium chloride complexesInfo
- Publication number
- GB823958A GB823958A GB14430/56A GB1443056A GB823958A GB 823958 A GB823958 A GB 823958A GB 14430/56 A GB14430/56 A GB 14430/56A GB 1443056 A GB1443056 A GB 1443056A GB 823958 A GB823958 A GB 823958A
- Authority
- GB
- United Kingdom
- Prior art keywords
- magnesium chloride
- chloride
- ethyl
- ether
- methyl
- 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
- -1 Organomagnesium chloride complexes Chemical class 0.000 title abstract 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 5
- CKCYDFVZAPRMBQ-UHFFFAOYSA-M [Cl-].CCCCCCCCCC[Mg+] Chemical compound [Cl-].CCCCCCCCCC[Mg+] CKCYDFVZAPRMBQ-UHFFFAOYSA-M 0.000 abstract 5
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 abstract 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 235000011147 magnesium chloride Nutrition 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 3
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 3
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 abstract 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- PTEYJUIKYIKULL-UHFFFAOYSA-N Ethyl pentadecanoate Chemical compound CCCCCCCCCCCCCCC(=O)OCC PTEYJUIKYIKULL-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 108010021119 Trichosanthin Proteins 0.000 abstract 2
- LRKYVRBDUIZJAS-UHFFFAOYSA-M [Cl-].C(CCCCCCCCCCCC)[Mg+] Chemical compound [Cl-].C(CCCCCCCCCCCC)[Mg+] LRKYVRBDUIZJAS-UHFFFAOYSA-M 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 abstract 2
- HQDAZWQQKSJCTM-UHFFFAOYSA-M magnesium;octane;chloride Chemical compound [Mg+2].[Cl-].CCCCCCC[CH2-] HQDAZWQQKSJCTM-UHFFFAOYSA-M 0.000 abstract 2
- CYSFUFRXDOAOMP-UHFFFAOYSA-M magnesium;prop-1-ene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C=C CYSFUFRXDOAOMP-UHFFFAOYSA-M 0.000 abstract 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 abstract 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 abstract 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 abstract 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 abstract 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 abstract 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 abstract 1
- YROGWJLGNLJNOK-UHFFFAOYSA-N 1-chloro-1-methoxypropane Chemical compound CCC(Cl)OC YROGWJLGNLJNOK-UHFFFAOYSA-N 0.000 abstract 1
- ASZMYJSJEOGSBR-UHFFFAOYSA-N 1-chlorotridecane Chemical compound CCCCCCCCCCCCCCl ASZMYJSJEOGSBR-UHFFFAOYSA-N 0.000 abstract 1
- DKZRLCHWDNEKRH-UHFFFAOYSA-N 1-nonoxynonane Chemical compound CCCCCCCCCOCCCCCCCCC DKZRLCHWDNEKRH-UHFFFAOYSA-N 0.000 abstract 1
- LOXRGHGHQYWXJK-UHFFFAOYSA-N 1-octylsulfanyloctane Chemical compound CCCCCCCCSCCCCCCCC LOXRGHGHQYWXJK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 abstract 1
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- VBCKYDVWOPZOBA-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxymethyl)oxolane Chemical compound C1CCOC1COCC1CCCO1 VBCKYDVWOPZOBA-UHFFFAOYSA-N 0.000 abstract 1
- WXSPHAQGTGMKEX-UHFFFAOYSA-N 2-benzyl-1,3-diphenylpropan-2-ol Chemical compound C=1C=CC=CC=1CC(CC=1C=CC=CC=1)(O)CC1=CC=CC=C1 WXSPHAQGTGMKEX-UHFFFAOYSA-N 0.000 abstract 1
- BTHLKLUTMYTDFM-UHFFFAOYSA-N 2-ethoxyoxane Chemical compound CCOC1CCCCO1 BTHLKLUTMYTDFM-UHFFFAOYSA-N 0.000 abstract 1
- BWEKDYGHDCHWEN-UHFFFAOYSA-N 2-methylhex-2-ene Chemical compound CCCC=C(C)C BWEKDYGHDCHWEN-UHFFFAOYSA-N 0.000 abstract 1
- UYOPRNGQFQWYER-UHFFFAOYSA-N 2-methylpent-4-en-2-ol Chemical compound CC(C)(O)CC=C UYOPRNGQFQWYER-UHFFFAOYSA-N 0.000 abstract 1
- WLPRUDLQOPCFNL-UHFFFAOYSA-N 2-methylpropane-1-sulfinic acid Chemical compound CC(C)CS(O)=O WLPRUDLQOPCFNL-UHFFFAOYSA-N 0.000 abstract 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 abstract 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- FKSAYGREWVVCIZ-UHFFFAOYSA-N 3-methyl-1-phenylbut-3-en-1-one Chemical compound CC(=C)CC(=O)C1=CC=CC=C1 FKSAYGREWVVCIZ-UHFFFAOYSA-N 0.000 abstract 1
- DAIQDVJAFRNVHH-UHFFFAOYSA-N 4-ethyl-3-methoxy-2-methyloctane Chemical compound COC(C(CCCC)CC)C(C)C DAIQDVJAFRNVHH-UHFFFAOYSA-N 0.000 abstract 1
- KUFDSEQTHICIIF-UHFFFAOYSA-N 6-methylhepta-1,5-diene Chemical compound CC(C)=CCCC=C KUFDSEQTHICIIF-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- XCXKZBWAKKPFCJ-UHFFFAOYSA-N Methyl-n-tetradecyl-keton Natural products CCCCCCCCCCCCCCC(C)=O XCXKZBWAKKPFCJ-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 abstract 1
- ITVZQOHDSSDZKU-UHFFFAOYSA-N [B+3].[O-]C.[O-]C.[O-]C Chemical compound [B+3].[O-]C.[O-]C.[O-]C ITVZQOHDSSDZKU-UHFFFAOYSA-N 0.000 abstract 1
- LICPNZOGRCGBTL-UHFFFAOYSA-M [Cl-].CC(C)=CC[Mg+] Chemical compound [Cl-].CC(C)=CC[Mg+] LICPNZOGRCGBTL-UHFFFAOYSA-M 0.000 abstract 1
- OJUNDVWJGXVXGJ-UHFFFAOYSA-M [Cl-].CCCCC(CC)C[Mg+] Chemical compound [Cl-].CCCCC(CC)C[Mg+] OJUNDVWJGXVXGJ-UHFFFAOYSA-M 0.000 abstract 1
- IAVOZFLTCYTHCY-UHFFFAOYSA-M [Cl-].CCCCCCC[Mg+] Chemical compound [Cl-].CCCCCCC[Mg+] IAVOZFLTCYTHCY-UHFFFAOYSA-M 0.000 abstract 1
- WMJMABVHDMRMJA-UHFFFAOYSA-M [Cl-].[Mg+]C1CCCCC1 Chemical compound [Cl-].[Mg+]C1CCCCC1 WMJMABVHDMRMJA-UHFFFAOYSA-M 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 abstract 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- ZTHQBROSBNNGPU-UHFFFAOYSA-M butyl sulfate(1-) Chemical compound CCCCOS([O-])(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-M 0.000 abstract 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 150000004292 cyclic ethers Chemical class 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- ZDABWEJSXJTEDB-UHFFFAOYSA-N decane-1-selenol Chemical compound C(CCCCCCCCC)[SeH] ZDABWEJSXJTEDB-UHFFFAOYSA-N 0.000 abstract 1
- WCKKWABZCCKDTN-UHFFFAOYSA-N decane-1-sulfonyl chloride Chemical compound CCCCCCCCCCS(Cl)(=O)=O WCKKWABZCCKDTN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 abstract 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 abstract 1
- NBEPJDWXROVPKA-UHFFFAOYSA-M magnesium;tetradecane;chloride Chemical compound [Mg+2].[Cl-].CCCCCCCCCCCCC[CH2-] NBEPJDWXROVPKA-UHFFFAOYSA-M 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000002734 organomagnesium group Chemical group 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052711 selenium Inorganic materials 0.000 abstract 1
- 239000011669 selenium Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- 229940087291 tridecyl alcohol Drugs 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002348 vinylic group Chemical group 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention comprises organomagnesium chloride complexes of formula R(MgCl.nQ)x, wherein n is an integer from 1 to 3, x is a small whole number, R is an aliphatic (other than vinylic), cycloaliphatic or aralkyl radical, the magnesium being bonded to a saturated carbon atom and Q is a substituted or unsubstituted cyclic ether having 5 or 6 atoms in the ring, the other ring atoms being carbon with the exception that a substituted nitrogen atom may replace the carbon atom in the 4 position when the ring has 6 atoms, the ring containing not more than one double bond and at least one carbon atom in the ring adjacent to the oxygen atom being free of substituents, the said ether containing no substituent reactive to the organo magnesium chloride or to any of the other components or products of the reaction mixture. Compounds within this definition include tetrahydrofuran, tetrahydropyran, 2-methyltetrahydrofuran, 2 - ethoxytetrahydropyran, tetrahydrofurfuryl ether, dihydropyran and N-methylmorpholine. The magnesium is reacted with the organic chloride in the presence of the compound Q which also acts as reaction medium; if necessary the reaction may be initiated by a small amount of ethyl bromide and/or ether and/or an iodine crystal. The complex may be broken by heating with a high boiling solvent such as xylene, cumene or kerosene, the compound Q distilling off until a solid (which contains residual amounts of Q) is obtained. The complex may be used in synthetic reactions to give alcohols, ketones, aldehydes, acetals, ketals, hydrocarbons, ethers, carboxylic acids (particularly acetic acid), esters, phenols, mercaptans, sulphinic acids, sulphoxides, sulphones, sulphides, disulphides, alkyl hydrogen selenides, alkyl hydrogen tellurides, organometallic compounds, or thio acids. Examples 1 to 22 inclusive describe the preparation of the tetrahydrofuran complexes of methyl, ethyl, n-propyl, isopropyl, tert.-butyl, isobutyl, sec.-butyl, n-hexyl, n-heptyl, cyclohexyl, n-octyl, n-decyl, n-lauryl, 2-ethylhexyl, n-octadecyl, cyclopentyl, 1 : 4 - cyclohexylene, 2,2 - difluoroethyl, 2,2 - difluoropropyl, benzyl, allyl and b -methallyl magnesium chlorides. The other examples describe (using the Grignard reagent as its complex with one or other of the specified Q compounds), the preparation of (23) allyldimethyl carbinol from allylmagnesium chloride and acetone; (24) dibutylundecylcarbinol from butyl magnesium chloride and methyl laurate; (25) methallylphenylketone and dimethallylphenyl carbinol from methallyl magnesium chloride and benzoyl chloride; (26) benzyl methyl ketone from benzyl magnesium chloride and acetonitrile; (27) nonylaldehyde diethyl acetal from n-octyl magnesium chloride and ethyl orthoformate; and phenyl acetaldehyde dimethyl acetal from benzyl magnesium chloride and methyl orthoformate; (28) 2-hexadecanone diethyl ketal from n-tetradecylmagnesium chloride and ethyl orthoacetate; (20) 2-cyclohexyl propanol-1 and 1-cyclohexylpropanol-2 from cyclohexylmagnesium chloride and propylene oxide; (30) 2-methyl hept-2,6-diene and 2 -methylhex-2-ene from isopent-2-en-1-yl magnesium chloride and allyl chloride and ethyl bromide respectively; and 1-tridecene from n -decyl magnesium chloride and allyl chloride; (31) n-tridecyl chloride from a -chloropropyl toluene sulphonate and n-decyl magnesium chloride; (32) 3-methyl heptane from sec.-butyl magnesium chloride and butyl sulphate: (33) methyl ethyl (2-ethyl hexyl) methyl ether from 2-ethyl hexyl magnesium chloride and ethyl chloromethyl methyl ether (itself prepared from hydrochloric acid, methanol and propionaldehyde); (34) di-n-nonyl ether from n-heptyl magnesium chloride and b ,b -dichloroethyl ether; di-iso-amyl ether from isopropyl magnesium chloride and b ,b 1-dichloroethyl ether; (35) ethyl pentadecanoate from n-tridecyl magnesium chloride and ethyl bromacetate; (36) benzyl mercaptan from benzyl magnesium chloride and powdered sulphur; (37) decyl hydrogen selenide from decyl magnesium chloride and powdered selenium; (38) n-amyl alcohol and tridecyl alcohol from oxygen and n-amyl magnesium chloride and tridecyl magnesium chloride respectively; (39) isobutyl sulphinic acid from isobutyl magnesium chloride and sulphur dioxide; (40) decyl sulphonyl chloride from n-decyl magnesium chloride and sulphuryl dichloride; (41) dioctyl sulphide from n-octyl magnesium chloride and sulphur monochloride; (42) triethyl aluminium from ethyl magnesium chloride and aluminium trichloride; tributyl tin chloride and tetrabutyl tin from butyl magnesium chloride and stannic chloride; tribenzyl antimony from benzyl magnesium chloride and antimony trichloride; triallyl boron from allylmagnesium chloride and boron trimethoxide; (43) phenyl acetic acid, dibenzyl ketone and tribenzyl carbinol from benzylmagnesium chloride and carbon dioxide; and (44) undecandithioic acid from decyl magnesium chloride and carbon disulphide. Specification 777,158 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US823958XA | 1955-11-28 | 1955-11-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB823958A true GB823958A (en) | 1959-11-18 |
Family
ID=22170927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14430/56A Expired GB823958A (en) | 1955-11-28 | 1956-05-09 | Organomagnesium chloride complexes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB823958A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006002691A1 (en) * | 2004-07-07 | 2006-01-12 | Lundbeck Pharmaceuticals Italy S.P.A. | Process for the synthesis and purification of (4-methoxybutyl) (4-trifluoromethylphenyl)methanone |
| WO2007099173A1 (en) * | 2006-03-03 | 2007-09-07 | Chemetall Gmbh | Organomagnesium synthesis agent |
| WO2014050273A1 (en) * | 2012-09-28 | 2014-04-03 | 住友精化株式会社 | Method for producing selenol |
| CN115124445A (en) * | 2022-01-25 | 2022-09-30 | 河南希百康健康产业有限公司 | Method for preparing L-selenomethylselenocysteine and L-selenocysteine with structure divergence |
-
1956
- 1956-05-09 GB GB14430/56A patent/GB823958A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006002691A1 (en) * | 2004-07-07 | 2006-01-12 | Lundbeck Pharmaceuticals Italy S.P.A. | Process for the synthesis and purification of (4-methoxybutyl) (4-trifluoromethylphenyl)methanone |
| WO2007099173A1 (en) * | 2006-03-03 | 2007-09-07 | Chemetall Gmbh | Organomagnesium synthesis agent |
| US20090173914A1 (en) * | 2006-03-03 | 2009-07-09 | Steffen Haber | Organomagnesium synthesis agent |
| US9534001B2 (en) * | 2006-03-03 | 2017-01-03 | Chemetall Gmbh | Organomagnesium synthesis agent |
| WO2014050273A1 (en) * | 2012-09-28 | 2014-04-03 | 住友精化株式会社 | Method for producing selenol |
| CN104520269A (en) * | 2012-09-28 | 2015-04-15 | 住友精化株式会社 | Method for producing selenol |
| JPWO2014050273A1 (en) * | 2012-09-28 | 2016-08-22 | 住友精化株式会社 | Method for producing selenols |
| CN115124445A (en) * | 2022-01-25 | 2022-09-30 | 河南希百康健康产业有限公司 | Method for preparing L-selenomethylselenocysteine and L-selenocysteine with structure divergence |
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