PT100005A - Processo para a preparacao de haletos de sulfonilo - Google Patents
Processo para a preparacao de haletos de sulfonilo Download PDFInfo
- Publication number
- PT100005A PT100005A PT100005A PT10000592A PT100005A PT 100005 A PT100005 A PT 100005A PT 100005 A PT100005 A PT 100005A PT 10000592 A PT10000592 A PT 10000592A PT 100005 A PT100005 A PT 100005A
- Authority
- PT
- Portugal
- Prior art keywords
- dimethyl
- preparation
- methyl
- chloride
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 18
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical class O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 title description 2
- -1 sulfenyl halide Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000002978 peroxides Chemical group 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000001030 gas--liquid chromatography Methods 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- MKLKDUHMZCIBSJ-UHFFFAOYSA-N methyl 3,3-dimethylpent-4-enoate Chemical compound COC(=O)CC(C)(C)C=C MKLKDUHMZCIBSJ-UHFFFAOYSA-N 0.000 description 5
- POMJJOMKSSKXJN-UHFFFAOYSA-N (1,1-dichloro-2,2,2-trifluoroethyl) thiohypochlorite Chemical compound FC(F)(F)C(Cl)(Cl)SCl POMJJOMKSSKXJN-UHFFFAOYSA-N 0.000 description 4
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- POFHGKISWXYKLB-UHFFFAOYSA-N methyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate Chemical compound COC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)Cl POFHGKISWXYKLB-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZDVBYNCJCIYCFO-UHFFFAOYSA-N 2,2,2-trifluoroethylsulfanylmethylbenzene Chemical compound FC(F)(F)CSCC1=CC=CC=C1 ZDVBYNCJCIYCFO-UHFFFAOYSA-N 0.000 description 3
- DKFGXLPITKDNNE-UHFFFAOYSA-N 4,6,6,6-tetrachloro-3,3-dimethylhexanoic acid Chemical compound OC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)Cl DKFGXLPITKDNNE-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- ZCPSWAFANXCCOT-UHFFFAOYSA-N trichloromethanesulfonyl chloride Chemical compound ClC(Cl)(Cl)S(Cl)(=O)=O ZCPSWAFANXCCOT-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PYZZTBGZBHXFIT-UHFFFAOYSA-N 1,1,1-trifluoro-2-(2,2,2-trifluoroethyldisulfanyl)ethane Chemical compound FC(F)(F)CSSCC(F)(F)F PYZZTBGZBHXFIT-UHFFFAOYSA-N 0.000 description 2
- VNEZTMDZQUSVFA-UHFFFAOYSA-N 1,1,2,2,2-pentachloroethanesulfonyl chloride Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)S(Cl)(=O)=O VNEZTMDZQUSVFA-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- YJAVURQFWVNFEC-UHFFFAOYSA-N dichloro-(4-chlorophenyl)methanesulfonyl chloride Chemical compound ClC1=CC=C(C(Cl)(Cl)S(Cl)(=O)=O)C=C1 YJAVURQFWVNFEC-UHFFFAOYSA-N 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- BNTZFXLKSXUEBE-UHFFFAOYSA-N methyl 4,6,6-trichloro-7,7,7-trifluoro-3,3-dimethylheptanoate Chemical compound COC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)C(F)(F)F BNTZFXLKSXUEBE-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002728 pyrethroid Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QCTAJIUIFMMQLM-UHFFFAOYSA-N (2,6-dichlorophenyl)methyl 4,6,6-trichloro-7,7,7-trifluoro-3,3-dimethylheptanoate Chemical compound FC(F)(F)C(Cl)(Cl)CC(Cl)C(C)(C)CC(=O)OCC1=C(Cl)C=CC=C1Cl QCTAJIUIFMMQLM-UHFFFAOYSA-N 0.000 description 1
- JCXJOIQSPVUAHQ-UHFFFAOYSA-N (2-methyl-3-phenylphenyl)methyl 4,6,6-trichloro-7,7,7-trifluoro-3,3-dimethylheptanoate Chemical compound CC1=C(COC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)C(F)(F)F)C=CC=C1C1=CC=CC=C1 JCXJOIQSPVUAHQ-UHFFFAOYSA-N 0.000 description 1
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- YDWKWNIVLRQNDZ-UHFFFAOYSA-N 1,1,2,2,2-pentachloroethyl thiohypochlorite Chemical compound ClSC(Cl)(Cl)C(Cl)(Cl)Cl YDWKWNIVLRQNDZ-UHFFFAOYSA-N 0.000 description 1
- NLYFGKQJZPUNAW-UHFFFAOYSA-N 1,1-dichloro-2,2,2-trifluoroethanesulfonyl chloride Chemical compound FC(F)(F)C(Cl)(Cl)S(Cl)(=O)=O NLYFGKQJZPUNAW-UHFFFAOYSA-N 0.000 description 1
- CXCHEKCRJQRVNG-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonyl chloride Chemical compound FC(F)(F)CS(Cl)(=O)=O CXCHEKCRJQRVNG-UHFFFAOYSA-N 0.000 description 1
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 1
- TZNJHEHAYZJBHR-UHFFFAOYSA-N 2-bromo-1,1,1-trifluoroethane Chemical compound FC(F)(F)CBr TZNJHEHAYZJBHR-UHFFFAOYSA-N 0.000 description 1
- REZPCHRHAYCMOS-UHFFFAOYSA-N 4,6,6-trichloro-7,7,7-trifluoro-3,3-dimethylheptanoic acid Chemical compound OC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)C(F)(F)F REZPCHRHAYCMOS-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- RHFDCPKFPABRDA-UHFFFAOYSA-N methyl 4,6,6,6-tetrabromo-3,3-dimethylhexanoate Chemical compound COC(=O)CC(C)(C)C(Br)CC(Br)(Br)Br RHFDCPKFPABRDA-UHFFFAOYSA-N 0.000 description 1
- HQPPFYOMIQTKHI-UHFFFAOYSA-N methyl 4,6,6,7,7,7-hexafluoro-3,3-dimethylheptanoate Chemical compound COC(=O)CC(C)(C)C(F)CC(F)(F)C(F)(F)F HQPPFYOMIQTKHI-UHFFFAOYSA-N 0.000 description 1
- JSFMWCVAHSCGDM-UHFFFAOYSA-N methyl 4-bromo-6,6,6-trifluoro-3,3-dimethylhexanoate Chemical compound COC(=O)CC(C)(C)C(Br)CC(F)(F)F JSFMWCVAHSCGDM-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UJLUNBBBWVVCPO-UHFFFAOYSA-N tribromomethanesulfonyl bromide Chemical compound BrC(Br)(Br)S(Br)(=O)=O UJLUNBBBWVVCPO-UHFFFAOYSA-N 0.000 description 1
- ZQHWXYHDFNLANF-UHFFFAOYSA-N tribromomethyl thiohypobromite Chemical compound BrSC(Br)(Br)Br ZQHWXYHDFNLANF-UHFFFAOYSA-N 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- IMNIECVIVJOTBH-UHFFFAOYSA-N trifluoromethanesulfonyl bromide Chemical compound FC(F)(F)S(Br)(=O)=O IMNIECVIVJOTBH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919100655A GB9100655D0 (en) | 1991-01-11 | 1991-01-11 | Preparation of sulphonyl halides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT100005A true PT100005A (pt) | 1993-01-29 |
Family
ID=10688326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT100005A PT100005A (pt) | 1991-01-11 | 1992-01-10 | Processo para a preparacao de haletos de sulfonilo |
Country Status (6)
| Country | Link |
|---|---|
| CN (1) | CN1063868A (cs) |
| AU (1) | AU1160992A (cs) |
| GB (2) | GB9100655D0 (cs) |
| PT (1) | PT100005A (cs) |
| TW (1) | TW215432B (cs) |
| WO (1) | WO1992012125A1 (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004155A (zh) * | 2019-09-11 | 2020-04-14 | 浙江埃森化学有限公司 | 一种三氟甲基亚磺酰卤的制备方法 |
| CN111116363B (zh) * | 2019-12-27 | 2023-04-14 | 山东潍坊润丰化工股份有限公司 | 一种羧酸酯类化合物的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2664443A (en) * | 1952-01-08 | 1953-12-29 | Olin Mathieson | Process of producing trichloromethane sulfonyl chloride |
| NL299822A (cs) * | 1962-10-29 | |||
| FR2599366B1 (fr) * | 1986-05-28 | 1988-08-26 | Rhone Poulenc Spec Chim | Procede de preparation du sulfure de benzyle et de trifluoromethyle |
| DE3741309A1 (de) * | 1987-12-05 | 1989-06-15 | Bayer Ag | Verfahren zur herstellung von trifluormethansulfonsaeurechlorid |
-
1991
- 1991-01-11 GB GB919100655A patent/GB9100655D0/en active Pending
-
1992
- 1992-01-08 AU AU11609/92A patent/AU1160992A/en not_active Abandoned
- 1992-01-08 GB GB9200266A patent/GB2251619A/en not_active Withdrawn
- 1992-01-08 WO PCT/GB1992/000038 patent/WO1992012125A1/en active Application Filing
- 1992-01-09 TW TW081100125A patent/TW215432B/zh active
- 1992-01-10 PT PT100005A patent/PT100005A/pt not_active Application Discontinuation
- 1992-01-11 CN CN92100864A patent/CN1063868A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB9100655D0 (en) | 1991-02-27 |
| WO1992012125A1 (en) | 1992-07-23 |
| CN1063868A (zh) | 1992-08-26 |
| GB2251619A (en) | 1992-07-15 |
| GB9200266D0 (en) | 1992-02-26 |
| TW215432B (cs) | 1993-11-01 |
| AU1160992A (en) | 1992-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB1A | Laying open of patent application |
Effective date: 19920917 |
|
| FC3A | Refusal |
Effective date: 19990311 |