JP6293622B2 - ジボランの除去方法およびジボラン除去剤 - Google Patents
ジボランの除去方法およびジボラン除去剤 Download PDFInfo
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- JP6293622B2 JP6293622B2 JP2014181381A JP2014181381A JP6293622B2 JP 6293622 B2 JP6293622 B2 JP 6293622B2 JP 2014181381 A JP2014181381 A JP 2014181381A JP 2014181381 A JP2014181381 A JP 2014181381A JP 6293622 B2 JP6293622 B2 JP 6293622B2
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- Prior art keywords
- diborane
- general formula
- formula
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- Prior art date
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- 238000000034 method Methods 0.000 title claims description 14
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 25
- -1 ketone compound Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910000085 borane Inorganic materials 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 229910015900 BF3 Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CHNLPLHJUPMEOI-UHFFFAOYSA-N oxolane;trifluoroborane Chemical compound FB(F)F.C1CCOC1 CHNLPLHJUPMEOI-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- KATOLVAXCGIBLO-UHFFFAOYSA-N 1,3-dibenzylurea Chemical compound C=1C=CC=CC=1CNC(=O)NCC1=CC=CC=C1 KATOLVAXCGIBLO-UHFFFAOYSA-N 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- XJLDYKIEURAVBW-UHFFFAOYSA-N 3-decanone Chemical compound CCCCCCCC(=O)CC XJLDYKIEURAVBW-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N 3-methyl-2-pentanone Chemical compound CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IYTXKIXETAELAV-UHFFFAOYSA-N Aethyl-n-hexyl-keton Natural products CCCCCCC(=O)CC IYTXKIXETAELAV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- TYBCSQFBSWACAA-UHFFFAOYSA-N Nonan-4-one Chemical compound CCCCCC(=O)CCC TYBCSQFBSWACAA-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YZBBUYKPTHDZHF-KNVGNIICSA-N (3R)-7,2'-dihydroxy-4'-methoxyisoflavanol Chemical compound OC1=CC(OC)=CC=C1[C@H]1C(O)C2=CC=C(O)C=C2OC1 YZBBUYKPTHDZHF-KNVGNIICSA-N 0.000 description 1
- ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 description 1
- YKQTUYZMOYXGKU-UHFFFAOYSA-N 1,1,3,3-tetrabenzylurea Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 YKQTUYZMOYXGKU-UHFFFAOYSA-N 0.000 description 1
- ZVWHURINXJWEER-UHFFFAOYSA-N 1,1,3,3-tetraphenylurea Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 ZVWHURINXJWEER-UHFFFAOYSA-N 0.000 description 1
- JZFDVPLHSQESAW-UHFFFAOYSA-N 1,1,3,3-tetrapropylurea Chemical compound CCCN(CCC)C(=O)N(CCC)CCC JZFDVPLHSQESAW-UHFFFAOYSA-N 0.000 description 1
- COSWCAGTKRUTQV-UHFFFAOYSA-N 1,1,3-trimethylurea Chemical compound CNC(=O)N(C)C COSWCAGTKRUTQV-UHFFFAOYSA-N 0.000 description 1
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- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- ZWAVGZYKJNOTPX-UHFFFAOYSA-N 1,3-diethylurea Chemical compound CCNC(=O)NCC ZWAVGZYKJNOTPX-UHFFFAOYSA-N 0.000 description 1
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- 229940057054 1,3-dimethylurea Drugs 0.000 description 1
- AWHORBWDEKTQAX-UHFFFAOYSA-N 1,3-dipropylurea Chemical compound CCCNC(=O)NCCC AWHORBWDEKTQAX-UHFFFAOYSA-N 0.000 description 1
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- VVCKMVBQLNBXOE-UHFFFAOYSA-N 3,3,4,4-tetramethyl-2-pentanone Chemical compound CC(=O)C(C)(C)C(C)(C)C VVCKMVBQLNBXOE-UHFFFAOYSA-N 0.000 description 1
- MQJUHFWPBZLKFV-UHFFFAOYSA-N 3,3,4-trimethylpentan-2-one Chemical compound CC(C)C(C)(C)C(C)=O MQJUHFWPBZLKFV-UHFFFAOYSA-N 0.000 description 1
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- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- VYXZFDDUSNDXNW-UHFFFAOYSA-N [K].CCOB(OCC)OCC Chemical compound [K].CCOB(OCC)OCC VYXZFDDUSNDXNW-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
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- AOZQADRDQYOZDE-UHFFFAOYSA-N acetonitrile;tribromoborane Chemical compound CC#N.BrB(Br)Br AOZQADRDQYOZDE-UHFFFAOYSA-N 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
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- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
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Images
Description
しかし、ボラン錯体を調製する場合、ボランが二量化してジボランを発生する。従来では、発生したジボランを別容器に入れたアセトン中に導入して除去する方法がとられていたが(非特許文献1)、アセトン単独ではジボランを完全に除去することは困難であり、除去しきれなかったジボランが反応系外にそのまま排出されて健康を害したり、爆発する恐れがあった。
式中、R3〜R9は各々独立して、水素原子、アルキル基、またはアリール基を表す。隣接した2つの基が結合して環を形成してもよい。
<2>ボラン錯体を用いる反応で発生するジボランを除去する前記<1>のジボランの除去方法。
<3>下記一般式(I)で表されるケトン化合物と、下記一般式(II)または一般式(III)で表される化合物とを含むジボラン除去剤。
本発明の方法は一般的なジボランの除去に有効であるが、特にボラン錯体を用いた合成反応で発生するジボランを除去するのに極めて効果的である。
本発明のボラン錯体とは、ボラン(BH3)とピリジンやアンモニア等の塩基、テトラヒドロフラン、ジメチルスルフィド、トリフェニルホスフィン等との錯体を示すが、これらに限定されない。
ボラン錯体は種々市販されており、入手も容易である。または公知の方法(例えば「実験化学講座 第4版」1992年刊、丸善 第20巻、72〜73頁等)で調製することも可能である。
用いる水素化ホウ素塩としては、具体的には水素化ホウ素リチウム、水素化ホウ素ナトリウム、水素化ホウ素カリウム、水素化ホウ素マグネシウム、水素化ホウ素カルシウム、水素化ホウ素アルミニウム、シアノ水素化ホウ素ナトリウム、水素化ホウ素亜鉛、水素化ホウ素ニッケル、水素化ホウ素アンモニウム、水素化トリメトキシホウ素リチウム、水素化トリメトキシホウ素ナトリウム、水素化トリメトキシホウ素カリウム、水素化トリエトキシホウ素リチウム、水素化トリエトキシホウ素ナトリウム、水素化トリエトキシホウ素カリウム、水素化トリエチルホウ素リチウム、水素化トリ(sec−ブチル)ホウ素リチウム、水素化トリ(sec−ブチル)ホウ素ナトリウム、水素化トリ(sec−ブチル)ホウ素カリウム等が挙げられる。
使用する三フッ化ホウ素の量は水素化ホウ素塩1molに対して、通常0.1〜10mol、好ましくは0.5〜5mol、より好ましくは0.5〜2molである。
一方、一般式(I)で表される化合物のみ(例えばアセトン単独)の場合、ジボランと反応はするが反応が遅く、そのため発生したジボランは全て除去しきれずに系外に放出されてしまっていると考えられる。
R1とR2とで結合して形成する環としては、シクロプロパン、シクロブタン、シクロペンタン、シクロヘキサン、シクロヘプタン等が挙げられる。
R3〜R5、R6〜R9の隣接した2つの基が結合して形成する環としては、ピロリジン、ピペリジン等が挙げられる。、
R1〜R9は更なる置換基を有していても良い。更なる置換基は、副反応が起きないものであれば特に制限は無いが、好ましくは炭素数1〜10の直鎖、分岐または環状のアルキル基、6〜10員環のアリール基が挙げられる。
これらの中でも好ましくは、アセトン、MEK、ジエチルケトンであり、より好ましくはアセトンである。
これらの中で好ましくはDMF、DMAc、N−メチルピロリドン、N−エチルピロリドンであり、より好ましくはDMF、DMAcである。
これらの中で好ましくはDMI、TMU、DMPUであり、より好ましくはDMIである。
一般式(II)または一般式(III)で表される化合物は、単独で使用しても、2種類以上を併用してもよい。これらの使用量は、基質や用いる装置によっても異なるが、本発明では一般式(I)で表されるケトン化合物との比率(v:v)で算出する。ケトン化合物と一般式(II)または一般式(III)で表される化合物との比率は、通常99.9:0.1〜50:50の範囲、好ましくは99.5:0.5〜70:30の範囲、より好ましくは97:3〜80:20の範囲である。
ジボランを除去する場合の温度は−10〜100℃、好ましくは−5〜50℃、より好ましくは0〜20℃である。
また、本発明において、前記除去剤を入れる装置は通常の合成実験で用いる器材や、化学合成を行う製造設備に設置されている装置をそのまま用いることができる。
窒素置換した300mlの四つ口フラスコに水素化ホウ素ナトリウム7.75g(204.9mmol)を入れ、続いてテトラヒドロフラン160mlを加えた。内温15℃以下に冷却し、13ml/分の窒素雰囲気下、攪拌しながら三フッ化ホウ素テトラヒドロフラン錯体33.75g(241.2mmol)を60分かけて滴下した。滴下開始直後に、四つ口フラスコ内のジボラン濃度を検知管で測定した。その後、四つ口フラスコから逆流防止用のクッションタンクを介し、ジボラン除去剤としてのアセトン240mlとDMAc60mlの混合溶媒の混合溶媒が入ったトラップへチューブを接続し、三フッ化ホウ素テトラヒドロフラン錯体滴下時に発生した気体をトラップ内でバブリングさせた(図1参照)。三フッ化ホウ素テトラヒドロフラン錯体滴下30分後と滴下終了後に、それぞれトラップから排気されたガス中のジボラン濃度を測定した。なお、上記の反応条件で発生するジボランの理論値は120.6mmolであった。
ジボラン除去剤を表1に示すものに変更した以外は、実施例1と同様の操作を行った。
ジボラン除去剤を表1に示すものに変更した以外は、実施例1と同様の操作を行った。実施例1〜6、比較例1〜2の結果を表1に示す。
Claims (3)
- ボラン錯体を合成する反応で発生するジボランを除去する請求項1のジボランの除去方法。
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