| 词条 | Fritsch–Buttenberg–Wiechell rearrangement |
| 释义 |
The Fritsch–Buttenberg–Wiechell rearrangement, named for Paul Ernst Moritz Fritsch (1859–1913), Wilhelm Paul Buttenberg, and Heinrich G. Wiechell, is a chemical reaction whereby a 1,1-diaryl-2-bromo-alkene rearranges to a 1,2-diaryl-alkyne by reaction with a strong base such as an alkoxide.[1][2][3] [4]This rearrangement is also possible with alkyl substituents.[5] Reaction MechanismThe strong base deprotonates the vinylic hydrogen, which after alpha-elimination forms a vinyl carbene. A 1,2-aryl migration forms the 1,2-diaryl-alkyne product. The mechanism of the FBW rearrangement was a subject of on-surface studies where the vinyl radical was visualised with sub-atomic resolution.[6] ScopeOne study explored this reaction for the synthesis of novel polyynes:[7][8] References1. ^{{cite journal | title = Ueber die Darstellung von Diphenylacetaldehyd und eine neue Synthese von Tolanderivaten | author = Paul Fritsch | journal = Justus Liebig's Annalen der Chemie | volume = 279 | issue = 3 | pages = 319–323 | year = 1894 | url = | doi = 10.1002/jlac.18942790310 }} 2. ^{{cite journal | title = Condensation des Dichloracetals mit Phenol und Toluol | author = Buttenberg, W. P. | journal = Justus Liebig's Annalen der Chemie | volume = 279 | issue = 3 | pages = 324–337 | year = 1894 | url = | doi = 10.1002/jlac.18942790311 }} 3. ^{{cite journal | title = Condensation des Dichloracetals mit Anisol und Phenetol | author = Wiechell, H. | journal = Justus Liebig's Annalen der Chemie | volume = 279 | issue = 3 | pages = 337–344 | year = 1894 | url = | doi = 10.1002/jlac.18942790312 }} 4. ^{{cite journal | title = Eliminations from Olefins | author = Köbrich, G. | journal = Angewandte Chemie International Edition | volume = 4 | issue = | pages = 49–68 | year = 1965 | url = | doi = 10.1002/anie.196500491 }} 5. ^{{cite journal | title = Fritsch-Buttenberg-Wiechell Rearrangement in the Aliphatic Series |author1=Rezaei, H. |author2=Yamanoi, S. |author3=Chemla, F. |author4=Normant, J. F. | journal = Org. Lett. | volume = 2 | issue = 4 | pages = 419–421 | year = 2000 | url = | doi = 10.1021/ol991117z }} 6. ^{{Cite journal|last=Pavliček|first=Niko|last2=Gawel|first2=Przemyslaw|last3=Kohn|first3=Daniel R.|last4=Majzik|first4=Zsolt|last5=Xiong|first5=Yaoyao|last6=Meyer|first6=Gerhard|last7=Anderson|first7=Harry L.|last8=Gross|first8=Leo|date=2018-07-02|title=Polyyne formation via skeletal rearrangement induced by atomic manipulation|url=https://doi.org/10.1038/s41557-018-0067-y|journal=Nature Chemistry|language=En|volume=10|issue=8|pages=853–858|doi=10.1038/s41557-018-0067-y|issn=1755-4330|pmc=6071858|pmid=29967394}} 7. ^One-Pot Formation and Derivatization of Di- and Triynes Based on the Fritsch-Buttenberg-Wiechell Rearrangement Thanh Luu, Yasuhiro Morisaki, Nina Cunningham, and Rik R. Tykwinski J. Org. Chem. 2007, 72, 9622–9629 {{DOI|10.1021/jo701810g}} 8. ^The metal acetylide intermediate is captured by electrophile methyl iodide. The reaction product is a biomolecule found in for instance Bidens pilosa 1. Darses, B.; Milet, A.; Philouze, C.; Greene, A. E.; Poisson, J.-F. o., Ynol Ethers from Dichloroenol Ethers: Mechanistic Elucidation Through 35Cl Labeling. Organic Letters 2008, 10 (20), 4445-4447. See also
2 : Rearrangement reactions|Name reactions |
| 随便看 |
|
开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。