JPS5912115B2 - β−ブロムアルキル−及びβ−ブロムアルケニルスルホンの製法 - Google Patents
β−ブロムアルキル−及びβ−ブロムアルケニルスルホンの製法Info
- Publication number
- JPS5912115B2 JPS5912115B2 JP50087429A JP8742975A JPS5912115B2 JP S5912115 B2 JPS5912115 B2 JP S5912115B2 JP 50087429 A JP50087429 A JP 50087429A JP 8742975 A JP8742975 A JP 8742975A JP S5912115 B2 JPS5912115 B2 JP S5912115B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- reaction
- mol
- methylsulfonyl
- 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
- 238000000034 method Methods 0.000 title description 12
- 230000008569 process Effects 0.000 title description 4
- 150000003457 sulfones Chemical class 0.000 title description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000002432 hydroperoxides Chemical class 0.000 claims description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
- 238000007259 addition reaction Methods 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 37
- 239000000203 mixture Substances 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- -1 sulfonic acid halide Chemical class 0.000 description 28
- 239000011592 zinc chloride Substances 0.000 description 26
- 235000005074 zinc chloride Nutrition 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000011002 quantification Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 19
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 16
- 150000001336 alkenes Chemical class 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 15
- ITYJDNHFRZSTJY-UHFFFAOYSA-N methanesulfonyl bromide Chemical compound CS(Br)(=O)=O ITYJDNHFRZSTJY-UHFFFAOYSA-N 0.000 description 15
- 238000009835 boiling Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- CGWWQPZGKPHLBU-UHFFFAOYSA-N benzenesulfonyl bromide Chemical compound BrS(=O)(=O)C1=CC=CC=C1 CGWWQPZGKPHLBU-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000006698 induction Effects 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000007269 dehydrobromination reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YOUYRGPEJNZDAY-UHFFFAOYSA-N 2-bromo-1,4-dimethoxy-3-methylsulfonylbutane Chemical compound COCC(Br)C(S(C)(=O)=O)COC YOUYRGPEJNZDAY-UHFFFAOYSA-N 0.000 description 3
- ZDTXCVNRZAWLNS-UHFFFAOYSA-N 3-bromo-4-methylsulfonyloxolane Chemical compound CS(=O)(=O)C1COCC1Br ZDTXCVNRZAWLNS-UHFFFAOYSA-N 0.000 description 3
- FSWCCQWDVGZMRD-UHFFFAOYSA-N 4-methylcyclohexene Chemical group CC1CCC=CC1 FSWCCQWDVGZMRD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XGXHQTOJAPGZNO-UHFFFAOYSA-N (1-bromo-1-ethoxy-2-methylpropan-2-yl)sulfonylbenzene Chemical compound CCOC(Br)C(C)(C)S(=O)(=O)C1=CC=CC=C1 XGXHQTOJAPGZNO-UHFFFAOYSA-N 0.000 description 2
- YBRAOJRURQGUAD-UHFFFAOYSA-N (1-bromo-2-methylsulfonylethyl)benzene Chemical compound CS(=O)(=O)CC(Br)C1=CC=CC=C1 YBRAOJRURQGUAD-UHFFFAOYSA-N 0.000 description 2
- IHCLUFSKPOJGDC-UHFFFAOYSA-N 1-ethoxy-2-methylprop-1-ene Chemical compound CCOC=C(C)C IHCLUFSKPOJGDC-UHFFFAOYSA-N 0.000 description 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- CIXRIBJXEHGURZ-UHFFFAOYSA-N 2-bromo-1-methylsulfonyloctane Chemical compound CCCCCCC(Br)CS(C)(=O)=O CIXRIBJXEHGURZ-UHFFFAOYSA-N 0.000 description 2
- XEKDTIOTHZWKGM-UHFFFAOYSA-N 3-(benzenesulfonyl)-2,5-dihydrofuran Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CCOC1 XEKDTIOTHZWKGM-UHFFFAOYSA-N 0.000 description 2
- UZPWKTCMUADILM-UHFFFAOYSA-N 3-methylcyclohexene Chemical group CC1CCCC=C1 UZPWKTCMUADILM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KWYMVQMYZBVTAZ-UHFFFAOYSA-N butane-1-sulfonyl bromide Chemical compound CCCCS(Br)(=O)=O KWYMVQMYZBVTAZ-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- KPWJBEFBFLRCLH-UHFFFAOYSA-L cadmium bromide Chemical compound Br[Cd]Br KPWJBEFBFLRCLH-UHFFFAOYSA-L 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910052716 thallium Inorganic materials 0.000 description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- XFRJQZKAXPXNGV-UHFFFAOYSA-N (2-bromo-3-methylsulfonylpropyl) acetate Chemical compound CC(=O)OCC(Br)CS(C)(=O)=O XFRJQZKAXPXNGV-UHFFFAOYSA-N 0.000 description 1
- VOPRTKOOBAUJAM-UHFFFAOYSA-N 1,1-dichloro-2-(2,2-dichloroethylsulfonyl)ethane Chemical compound ClC(Cl)CS(=O)(=O)CC(Cl)Cl VOPRTKOOBAUJAM-UHFFFAOYSA-N 0.000 description 1
- VXTYNAYYDYWUSP-UHFFFAOYSA-N 1,1-ditert-butyl-4-(4,4-ditert-butylcyclohexyl)peroxycyclohexane Chemical compound C(C)(C)(C)C1(CCC(CC1)OOC1CCC(CC1)(C(C)(C)C)C(C)(C)C)C(C)(C)C VXTYNAYYDYWUSP-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QGSGLXROCJEJCW-UHFFFAOYSA-N 1-bromo-2-butylsulfonylcyclohexane Chemical compound CCCCS(=O)(=O)C1CCCCC1Br QGSGLXROCJEJCW-UHFFFAOYSA-N 0.000 description 1
- ZBMNTXBCLASLSW-UHFFFAOYSA-N 1-bromo-2-methylsulfonylcycloheptane Chemical compound CS(=O)(=O)C1CCCCCC1Br ZBMNTXBCLASLSW-UHFFFAOYSA-N 0.000 description 1
- UOXYNCDQUYPYRY-UHFFFAOYSA-N 1-bromo-2-methylsulfonylcyclohexane Chemical compound CS(=O)(=O)C1CCCCC1Br UOXYNCDQUYPYRY-UHFFFAOYSA-N 0.000 description 1
- PAXBWAGGHZYOIS-UHFFFAOYSA-N 1-bromo-4-methyl-2-methylsulfonylcyclohexane Chemical compound CC1CCC(Br)C(S(C)(=O)=O)C1 PAXBWAGGHZYOIS-UHFFFAOYSA-N 0.000 description 1
- KTNXZNRAHFETOD-UHFFFAOYSA-N 1-butylsulfonylcyclohexene Chemical compound CCCCS(=O)(=O)C1=CCCCC1 KTNXZNRAHFETOD-UHFFFAOYSA-N 0.000 description 1
- BQAALRDBKOCJSE-UHFFFAOYSA-N 1-hydroperoxy-2,3-dihydro-1h-indene Chemical compound C1=CC=C2C(OO)CCC2=C1 BQAALRDBKOCJSE-UHFFFAOYSA-N 0.000 description 1
- USVYTUVHEVKZSX-UHFFFAOYSA-N 1-methylsulfonylcyclohexene Chemical compound CS(=O)(=O)C1=CCCCC1 USVYTUVHEVKZSX-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- JITPLZPWKYUTDM-UHFFFAOYSA-N 1-phenylprop-2-yn-1-one Chemical compound C#CC(=O)C1=CC=CC=C1 JITPLZPWKYUTDM-UHFFFAOYSA-N 0.000 description 1
- GXCBGPWGHZAONS-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-methylpropanal Chemical compound O=CC(C)(C)S(=O)(=O)C1=CC=CC=C1 GXCBGPWGHZAONS-UHFFFAOYSA-N 0.000 description 1
- VGIWSFWOJJDQAR-UHFFFAOYSA-N 2-(benzenesulfonyl)ethynylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C#CC1=CC=CC=C1 VGIWSFWOJJDQAR-UHFFFAOYSA-N 0.000 description 1
- CBEDHUWRUQKFEX-UHFFFAOYSA-N 2-bromooxolane Chemical compound BrC1CCCO1 CBEDHUWRUQKFEX-UHFFFAOYSA-N 0.000 description 1
- JSZPBTUOIOMFMS-UHFFFAOYSA-N 2-hydroperoxyoxolane Chemical compound OOC1CCCO1 JSZPBTUOIOMFMS-UHFFFAOYSA-N 0.000 description 1
- RJQJJDKSNFBCFC-UHFFFAOYSA-N 2-methylsulfonylethenylbenzene Chemical compound CS(=O)(=O)C=CC1=CC=CC=C1 RJQJJDKSNFBCFC-UHFFFAOYSA-N 0.000 description 1
- MDKMCOCEBTZOJS-UHFFFAOYSA-N 3-(4-nitrophenyl)sulfonyl-2,5-dihydrofuran Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)C1=CCOC1 MDKMCOCEBTZOJS-UHFFFAOYSA-N 0.000 description 1
- FONBYZBCFVFQBU-UHFFFAOYSA-N 3-(benzenesulfonyl)-4-bromooxolane Chemical compound BrC1COCC1S(=O)(=O)C1=CC=CC=C1 FONBYZBCFVFQBU-UHFFFAOYSA-N 0.000 description 1
- PJZAMFVGIXVDEX-UHFFFAOYSA-N 3-bromo-4-(chloromethylsulfonyl)oxolane Chemical compound ClCS(=O)(=O)C1COCC1Br PJZAMFVGIXVDEX-UHFFFAOYSA-N 0.000 description 1
- WYWOOCCJDYNXJH-UHFFFAOYSA-N 3-bromo-4-ethylsulfonyloxolane Chemical compound CCS(=O)(=O)C1COCC1Br WYWOOCCJDYNXJH-UHFFFAOYSA-N 0.000 description 1
- WCMSFBRREKZZFL-UHFFFAOYSA-N 3-cyclohexen-1-yl-Benzene Chemical compound C1CCCC(C=2C=CC=CC=2)=C1 WCMSFBRREKZZFL-UHFFFAOYSA-N 0.000 description 1
- NQTWCUHEDHPHDW-UHFFFAOYSA-N 3-ethylsulfonyl-2,5-dihydrofuran Chemical compound CCS(=O)(=O)C1=CCOC1 NQTWCUHEDHPHDW-UHFFFAOYSA-N 0.000 description 1
- HHWUOZJEHMOHSE-UHFFFAOYSA-N 3-methylsulfonyloxolane Chemical compound CS(=O)(=O)C1CCOC1 HHWUOZJEHMOHSE-UHFFFAOYSA-N 0.000 description 1
- KMUJKZAILNPRBI-UHFFFAOYSA-N 3-methylsulfonylprop-2-enyl acetate Chemical compound CC(=O)OCC=CS(C)(=O)=O KMUJKZAILNPRBI-UHFFFAOYSA-N 0.000 description 1
- MWWVGPAAMFWVKJ-UHFFFAOYSA-N 4-methyl-1-methylsulfonylcyclohexene Chemical compound CC1CCC(S(C)(=O)=O)=CC1 MWWVGPAAMFWVKJ-UHFFFAOYSA-N 0.000 description 1
- SEMFFDCKIIAGQP-UHFFFAOYSA-N 4-nitrobenzenesulfonyl bromide Chemical compound [O-][N+](=O)C1=CC=C(S(Br)(=O)=O)C=C1 SEMFFDCKIIAGQP-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- KJKWCMBULINIGT-UHFFFAOYSA-N 5-methyl-1-methylsulfonylcyclohexene Chemical compound CC1CCC=C(S(C)(=O)=O)C1 KJKWCMBULINIGT-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical class [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- KZEKKKHNXUUYJO-UHFFFAOYSA-N [2-(benzenesulfonyl)-1-bromoethenyl]benzene Chemical compound C=1C=CC=CC=1C(Br)=CS(=O)(=O)C1=CC=CC=C1 KZEKKKHNXUUYJO-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- LHQLJMJLROMYRN-UHFFFAOYSA-L cadmium acetate Chemical compound [Cd+2].CC([O-])=O.CC([O-])=O LHQLJMJLROMYRN-UHFFFAOYSA-L 0.000 description 1
- XIEPJMXMMWZAAV-UHFFFAOYSA-N cadmium nitrate Inorganic materials [Cd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XIEPJMXMMWZAAV-UHFFFAOYSA-N 0.000 description 1
- QCUOBSQYDGUHHT-UHFFFAOYSA-L cadmium sulfate Chemical compound [Cd+2].[O-]S([O-])(=O)=O QCUOBSQYDGUHHT-UHFFFAOYSA-L 0.000 description 1
- 229910000331 cadmium sulfate Inorganic materials 0.000 description 1
- NRGIRRZWCDKDMV-UHFFFAOYSA-H cadmium(2+);diphosphate Chemical compound [Cd+2].[Cd+2].[Cd+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O NRGIRRZWCDKDMV-UHFFFAOYSA-H 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical class S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- ZYZWOSIRFVIBRH-UHFFFAOYSA-N chloroform;cyclohexane Chemical compound ClC(Cl)Cl.C1CCCCC1 ZYZWOSIRFVIBRH-UHFFFAOYSA-N 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- OJVUCGARLMOOCV-UHFFFAOYSA-N chloromethanesulfonyl bromide Chemical compound ClCS(Br)(=O)=O OJVUCGARLMOOCV-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- PQXXMTMCMCKPCG-UHFFFAOYSA-N cyclohexen-1-ylsulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CCCCC1 PQXXMTMCMCKPCG-UHFFFAOYSA-N 0.000 description 1
- MUGCFKANMVCDNO-UHFFFAOYSA-N cyclohexene;hydrogen peroxide Chemical compound OO.C1CCC=CC1 MUGCFKANMVCDNO-UHFFFAOYSA-N 0.000 description 1
- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- FJKFBLLIOVQLFS-UHFFFAOYSA-L dibenzoyloxymercury Chemical compound [Hg+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 FJKFBLLIOVQLFS-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- LYCAETJDIBWXOF-UHFFFAOYSA-N ethoxyethane;hydrogen peroxide Chemical compound OO.CCOCC LYCAETJDIBWXOF-UHFFFAOYSA-N 0.000 description 1
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- PNOYFOCGOOMIFJ-PLNGDYQASA-N methyl (z)-3-methylsulfonylbut-2-enoate Chemical compound COC(=O)\C=C(\C)S(C)(=O)=O PNOYFOCGOOMIFJ-PLNGDYQASA-N 0.000 description 1
- LYHAFGXRDMZEGW-UHFFFAOYSA-N methyl 2-bromo-3-methylsulfonylbutanoate Chemical compound COC(=O)C(Br)C(C)S(C)(=O)=O LYHAFGXRDMZEGW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 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
- 150000002825 nitriles Chemical class 0.000 description 1
- UMIPWJGWASORKV-UHFFFAOYSA-N oct-1-yne Chemical compound CCCCCCC#C UMIPWJGWASORKV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical compound CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-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
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ZCPSWAFANXCCOT-UHFFFAOYSA-N trichloromethanesulfonyl chloride Chemical compound ClC(Cl)(Cl)S(Cl)(=O)=O ZCPSWAFANXCCOT-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2435098A DE2435098C3 (de) | 1974-07-22 | 1974-07-22 | Verfahren zur Herstellung von ß- Bromalkyl- und ß-Bromalkenylsulfonen |
| DE2435098 | 1974-07-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5136421A JPS5136421A (en) | 1976-03-27 |
| JPS5912115B2 true JPS5912115B2 (ja) | 1984-03-21 |
Family
ID=5921146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50087429A Expired JPS5912115B2 (ja) | 1974-07-22 | 1975-07-18 | β−ブロムアルキル−及びβ−ブロムアルケニルスルホンの製法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4022804A (enExample) |
| JP (1) | JPS5912115B2 (enExample) |
| AT (1) | AT340375B (enExample) |
| BE (1) | BE831597A (enExample) |
| CA (1) | CA1076593A (enExample) |
| CH (1) | CH612419A5 (enExample) |
| DE (1) | DE2435098C3 (enExample) |
| FR (1) | FR2279727A1 (enExample) |
| GB (1) | GB1505922A (enExample) |
| HU (1) | HU171405B (enExample) |
| NL (1) | NL7508585A (enExample) |
| YU (1) | YU186275A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2935682A1 (de) * | 1979-09-04 | 1981-03-12 | Bayer Ag, 5090 Leverkusen | Carbonsaeurederivate. |
| US4604480A (en) * | 1983-08-15 | 1986-08-05 | The Research Foundation Of State University Of New York | Method for the preparation of sulfones and compounds containing carbon chains having conjugated unsaturation and the compounds resulting from such method |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573580A (en) * | 1949-03-23 | 1951-10-30 | Us Rubber Co | Preparation of aromatic sulfones |
-
1974
- 1974-07-22 DE DE2435098A patent/DE2435098C3/de not_active Expired
-
1975
- 1975-07-11 CA CA231,424A patent/CA1076593A/en not_active Expired
- 1975-07-16 US US05/596,305 patent/US4022804A/en not_active Expired - Lifetime
- 1975-07-17 CH CH940275A patent/CH612419A5/xx not_active IP Right Cessation
- 1975-07-17 NL NL7508585A patent/NL7508585A/xx not_active Application Discontinuation
- 1975-07-18 JP JP50087429A patent/JPS5912115B2/ja not_active Expired
- 1975-07-21 AT AT561275A patent/AT340375B/de active
- 1975-07-21 GB GB30379/75A patent/GB1505922A/en not_active Expired
- 1975-07-21 FR FR7522685A patent/FR2279727A1/fr active Granted
- 1975-07-21 HU HU75BA00003306A patent/HU171405B/hu unknown
- 1975-07-22 BE BE158490A patent/BE831597A/xx not_active IP Right Cessation
- 1975-07-22 YU YU01862/75A patent/YU186275A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2435098A1 (de) | 1976-02-12 |
| CA1076593A (en) | 1980-04-29 |
| HU171405B (hu) | 1978-01-28 |
| FR2279727A1 (fr) | 1976-02-20 |
| DE2435098B2 (de) | 1977-12-15 |
| NL7508585A (nl) | 1976-01-26 |
| GB1505922A (en) | 1978-04-05 |
| BE831597A (fr) | 1976-01-22 |
| ATA561275A (de) | 1977-04-15 |
| CH612419A5 (enExample) | 1979-07-31 |
| FR2279727B1 (enExample) | 1980-04-30 |
| YU186275A (en) | 1982-02-28 |
| JPS5136421A (en) | 1976-03-27 |
| US4022804A (en) | 1977-05-10 |
| AT340375B (de) | 1977-12-12 |
| DE2435098C3 (de) | 1978-08-10 |
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