| 词条 | Borane–tetrahydrofuran |
| 释义 |
| Name = | ImageFileL1 = Bh3-thf-complex.png | ImageFileR1 = Borane-THF-adduct-3D-balls.png | IUPACName = | OtherNames = |Section1={{Chembox Identifiers | CASNo = 14044-65-6 | PubChem = 11062302 | EC_number = 237-881-8 | UNII = 5EAR4ERR1L | ChemSpiderID = | StdInChI=1S/C4H8O.B/c1-2-4-5-3-1;/h1-4H2; | StdInChIKey = UWTDFICHZKXYAC-UHFFFAOYSA-N | SMILES = [BH3-][O+]1CCCC1 |Section2={{Chembox Properties | C=4 | H=11 | B=1 | O=1 | Appearance = White solid | Density = | MeltingPtC = 66 | MeltingPt_ref = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPtC = -17 | GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|225|260|302|315|318|319|335}} | PPhrases = {{P-phrases|210|223|231+232|233|240|241|242|243|261|264|270|271|280|301+312|302+352|303+361+353|304+340|305+351+338|310|312|321|330|332+313|335+334|337+313|362|370+378|402+404|403+233|403+235|405|501}} | AutoignitionPt = }}Borane–tetrahydrofuran is a dipolar bond charge-transfer complex composed of borane and tetrahydrofuran (THF). These solutions are used for reductions and hydroboration, reactions that are useful in synthesis of organic compounds.[1] Preparation and usesThe complex is commercially available but can also be generated by the dissolution of diborane in THF. A practical route to this is the oxidation of sodium borohydride with iodine in THF.[2] The complex can reduce carboxylic acids to alcohols and is a common route for the reduction of amino acids to amino alcohols[3] (e.g. valinol). It adds across alkenes to give organoboron compounds that are useful intermediates.[4] The following organoboron reagents are prepared from borane-THF: 9-borabicyclo[3.3.1]nonane, Alpine borane, diisopinocampheylborane. It is also used as a source of borane (BH3) for the formation of adducts.[5] SafetyThe solution is highly sensitive to air, requiring the use of air-free techniques.[1] See also
References1. ^1 Marek Zaidlewicz, Herbert C. Brown, Santhosh F. Neelamkavil, "Borane–Tetrahydrofuran" Encyclopedia of Reagents for Organic Synthesis, 2008 John Wiley & Sons. {{DOI|10.1002/047084289X.rb241.pub2}} {{DEFAULTSORT:Borane-tetrahydrofuran}}2. ^{{cite journal|last=Kanth|first=J. V. Bhaskar|author2=Periasamy, Mariappan |title=Selective reduction of carboxylic acids into alcohols using sodium borohydride and iodine|journal=The Journal of Organic Chemistry|date=1 September 1991|volume=56|issue=20|pages=5964–5965|doi=10.1021/jo00020a052}} 3. ^{{cite journal|last1=McKennon|first1=Marc J.|last2=Meyers|first2=A. I.|last3=Drauz|first3=Karlheinz|last4=Schwarm|first4=Michael|title=A convenient reduction of amino acids and their derivatives|journal=The Journal of Organic Chemistry|date=June 1993|volume=58|issue=13|pages=3568–3571|doi=10.1021/jo00065a020}} 4. ^{{OrgSynth |first1= George W. |last1= Kabalka |first2= John T. |last2= Maddox |first3= Timothy |last3= Shoup |first4= Karla R. |last4= Bowers |title= A Simple And Convenient Method For The Oxidation Of Organoboranes Using Sodium Perborate: (+)-isopinocampheol | year= 1996 |volume= 73 |pages= 116 |prep= CV9P0522 }} 5. ^{{OrgSynth |first1= Karen V. L. |last1= Crépy |first2= Tsuneo |last2= Imamoto |title= Preparation Of (S,S)-1,2-Bis-(tert-butylmethylphosphino)ethane ((S,S)-t-Bu-BISP*) As A Rhodium Complex |year= 2005 |volume= 82 |pages= 22 |prep= v82p0022 }} 2 : Boranes|Reagents for organic chemistry |
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