CN1303386A - 碱金属取代氢硼化物试剂的合成方法 - Google Patents
碱金属取代氢硼化物试剂的合成方法 Download PDFInfo
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- CN1303386A CN1303386A CN99806695.8A CN99806695A CN1303386A CN 1303386 A CN1303386 A CN 1303386A CN 99806695 A CN99806695 A CN 99806695A CN 1303386 A CN1303386 A CN 1303386A
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- Prior art keywords
- alkali metal
- sec
- tri
- formula
- trisubstituted
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- 229910052783 alkali metal Inorganic materials 0.000 title claims abstract description 77
- 150000001340 alkali metals Chemical group 0.000 title claims abstract description 75
- 239000003153 chemical reaction reagent Substances 0.000 title abstract description 20
- 230000015572 biosynthetic process Effects 0.000 title description 10
- 238000003786 synthesis reaction Methods 0.000 title description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 89
- 238000006243 chemical reaction Methods 0.000 claims abstract description 76
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000011591 potassium Substances 0.000 claims abstract description 57
- 229910000085 borane Inorganic materials 0.000 claims abstract description 31
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims abstract description 31
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims abstract description 25
- 230000008569 process Effects 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000000852 hydrogen donor Substances 0.000 claims abstract description 20
- 239000007787 solid Substances 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- YUPAWYWJNZDARM-UHFFFAOYSA-N tri(butan-2-yl)borane Chemical group CCC(C)B(C(C)CC)C(C)CC YUPAWYWJNZDARM-UHFFFAOYSA-N 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 38
- -1 lithium tri-sec-butylborohydride Chemical compound 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000011734 sodium Substances 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 21
- 229910052708 sodium Inorganic materials 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052744 lithium Inorganic materials 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 13
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 229910052792 caesium Inorganic materials 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 7
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 claims description 6
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 239000012454 non-polar solvent Substances 0.000 claims description 5
- SJXLNIDKIYXLBL-UHFFFAOYSA-N tricyclohexylborane Chemical compound C1CCCCC1B(C1CCCCC1)C1CCCCC1 SJXLNIDKIYXLBL-UHFFFAOYSA-N 0.000 claims description 5
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- ZTKBVWUYLHTIBB-UHFFFAOYSA-N tri(propan-2-yl)borane Chemical compound CC(C)B(C(C)C)C(C)C ZTKBVWUYLHTIBB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- LFXWJXWPMAPFOU-UHFFFAOYSA-N tripentylborane Chemical compound CCCCCB(CCCCC)CCCCC LFXWJXWPMAPFOU-UHFFFAOYSA-N 0.000 claims description 3
- WWAQGQQCCPPDNR-UHFFFAOYSA-N 9-propan-2-yloxy-9-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1B2OC(C)C WWAQGQQCCPPDNR-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 abstract description 13
- 150000008046 alkali metal hydrides Chemical class 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 126
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 28
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 28
- 238000004607 11B NMR spectroscopy Methods 0.000 description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 17
- 230000005587 bubbling Effects 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 13
- 229910000574 NaK Inorganic materials 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- 229910000105 potassium hydride Inorganic materials 0.000 description 4
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000005649 metathesis reaction Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229910003074 TiCl4 Inorganic materials 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 229910000103 lithium hydride Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 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 description 1
- VCDGSBJCRYTLNU-NYCFMAHJSA-N 9-[(1s,3s,4r,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]-9-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1B2[C@H]1C[C@H](C2(C)C)C[C@H]2[C@@H]1C VCDGSBJCRYTLNU-NYCFMAHJSA-N 0.000 description 1
- XYGKGASSKJWLTN-UHFFFAOYSA-N CCCCCCC.CCCCCCC Chemical compound CCCCCCC.CCCCCCC XYGKGASSKJWLTN-UHFFFAOYSA-N 0.000 description 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- FBHSUABQCRNUDW-UHFFFAOYSA-N [K].CCCCCCCCC Chemical compound [K].CCCCCCCCC FBHSUABQCRNUDW-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 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 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- UZMMTBDONLVQMH-UHFFFAOYSA-N tris(3-methylbutan-2-yl)borane Chemical compound CC(C)C(C)B(C(C)C(C)C)C(C)C(C)C UZMMTBDONLVQMH-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
催化剂(克) | 金属钾(摩尔) | TSBB(摩尔) | 温度(℃) | 产率 |
无 | 0.424 | 0.354 | 85 | 94% |
无 | 0.393 | 0.403 | 85 | 89% |
无 | 0.3541.7% | 0.348 | 85 | 88% |
0.71萘 | 0.348 | 0.346 | 85 | - |
1石墨 | 0.348 | 0.34 | 85 | 62% |
1菲1.60%摩尔 | 0.3499 | 0.385 | 85 | 81% |
0.25菲0.4%摩尔 | 0.348 | 0.34 | 75 | 84% |
0.5菲0.8%摩尔 | 0.348 | 0.34 | 75 | 92% |
0.5菲1.6%摩尔 | 0.174 | 0.17 | 75 | 87% |
金属钾[摩尔]eq | TSBB[摩尔] | 溶剂 | 温度[℃] | H2[psig] | 经11B-NMR测得的%KTSBBH(产率) |
0.4841.2 | 0.403 | 二甲氧基乙烷(monoglyme) | 84-90 | 50 | 90 |
0.421.2 | 0.35 | 二甲氧基乙烷(monoglyme) | 86 | 0(41 psigN2) | 78 |
0.4841.2 | 0.403 | 甲苯 | 84 | 50 | 75 |
0.42431.2 | 0.3537 | THF | 83 | 50 | 94 |
硼烷 | 产率(%)(按11B-NMR计) |
B(仲丁基)3 | 88-94 |
BEt3 | 42 |
B(环己基)3 | 71 |
BPh3 | 50 |
(S)-B-异松蒎基-9-硼杂双环[3.3.1]壬烷 | 48 |
9-异丙氧基-9-BBN | 85 |
B(异丙氧基)3 | 16 |
金属[摩尔](eq) | TSBB[摩尔] | 温度[℃] | 经11B-NMR测得并按硼化合物总量计算的%KTSBBH(产率) |
NaK[0.2Na][0.43K] | 0.359 | 85 | 95 |
NaK[0.0951Na][0.2K] | 0.3 | 85 | 57 |
K+Na0.3069K(1.2 eq)0.0035 Na | 0.256 | 84 | 81.6 |
NaK[0.19Na][0.396K] | 0.329 | 42 | 69 |
催化剂 | 按11B-NMR测得的%KTSBBH |
菲 | 96.5 |
丁烯 | - |
无 | 29 |
无 | 18 |
苯并[9,10]菲 | 87 |
芘 | 24 |
萘 | 24 |
反应物 | 按11B-NMR测得的%KTSBBH |
三仲丁基硼烷 | 96.5% |
三乙基硼烷 | 90% |
三异丙基硼烷 | 90% |
溶剂 | 按11B-NMR测得的%KTSBBH |
THF | 96.5% |
辛烷 | 91%(分离的KTSBBH固体) |
庚烷 | 95%(分离的KTSBBH固体) |
C | H | B | K | 总计 | |
克/摩尔KTSBBH | 144.13 | 28.22 | 10.81 | 39.09 | 222.252 |
理论%重量 | 64.85 | 12.70 | 4.86 | 17.59 | 99.99 |
试验1的实测%重量 | 61.28 | 12.26 | 5.88 | 16.88 | 95.9 |
试验2的实测%重量 | 63.37 | 12.96 | 5.36 | 17.06 | 98.75 |
Claims (39)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1999/001076 WO2000043400A1 (en) | 1999-01-19 | 1999-01-19 | Synthesis of alkali metal substituted borohydride reagents |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1303386A true CN1303386A (zh) | 2001-07-11 |
CN1145631C CN1145631C (zh) | 2004-04-14 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB998066958A Expired - Fee Related CN1145631C (zh) | 1999-01-19 | 1999-01-19 | 碱金属取代氢硼化物试剂的合成方法 |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1144419B1 (zh) |
JP (1) | JP4536931B2 (zh) |
CN (1) | CN1145631C (zh) |
AT (1) | ATE275568T1 (zh) |
AU (1) | AU2236499A (zh) |
DE (1) | DE69920049T2 (zh) |
WO (1) | WO2000043400A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7718154B2 (en) | 2005-06-16 | 2010-05-18 | Air Products And Chemicals, Inc. | Process for producing boranes |
CN115011977A (zh) * | 2022-07-25 | 2022-09-06 | 南京工业大学 | 一种利用微反应装置连续电合成吲哚啉类化合物的方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113481383B (zh) * | 2021-07-21 | 2022-07-19 | 合肥学院 | 一种金属钾的制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1717160A1 (de) * | 1968-02-10 | 1971-08-05 | Schloemann Ag | Verfahren zur Herstellung von Alkalimetallhydrid |
DE2722221A1 (de) * | 1977-05-17 | 1978-11-23 | Studiengesellschaft Kohle Mbh | Alkalimetallkomplexverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur hydrierung und nitridierung von alkalimetallen |
FR2532290A1 (fr) * | 1982-08-31 | 1984-03-02 | Rhone Poulenc Spec Chim | Procede et dispositif d'hydrogenation en continu du lithium dans un melange de sels fondus |
US5186868A (en) * | 1990-04-05 | 1993-02-16 | The Regents Of The University Of California | Methods for tritium labeling |
FR2749847B1 (fr) * | 1996-06-13 | 1998-11-06 | Expansia Sa | Organoboranes chiraux |
-
1999
- 1999-01-19 DE DE69920049T patent/DE69920049T2/de not_active Expired - Lifetime
- 1999-01-19 AU AU22364/99A patent/AU2236499A/en not_active Abandoned
- 1999-01-19 CN CNB998066958A patent/CN1145631C/zh not_active Expired - Fee Related
- 1999-01-19 AT AT99902363T patent/ATE275568T1/de not_active IP Right Cessation
- 1999-01-19 WO PCT/US1999/001076 patent/WO2000043400A1/en active IP Right Grant
- 1999-01-19 JP JP2000594816A patent/JP4536931B2/ja not_active Expired - Fee Related
- 1999-01-19 EP EP99902363A patent/EP1144419B1/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7718154B2 (en) | 2005-06-16 | 2010-05-18 | Air Products And Chemicals, Inc. | Process for producing boranes |
CN115011977A (zh) * | 2022-07-25 | 2022-09-06 | 南京工业大学 | 一种利用微反应装置连续电合成吲哚啉类化合物的方法 |
Also Published As
Publication number | Publication date |
---|---|
JP4536931B2 (ja) | 2010-09-01 |
JP2002535336A (ja) | 2002-10-22 |
ATE275568T1 (de) | 2004-09-15 |
AU2236499A (en) | 2000-08-07 |
EP1144419A1 (en) | 2001-10-17 |
EP1144419B1 (en) | 2004-09-08 |
WO2000043400A1 (en) | 2000-07-27 |
DE69920049T2 (de) | 2005-01-20 |
CN1145631C (zh) | 2004-04-14 |
DE69920049D1 (de) | 2004-10-14 |
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