| 词条 | Grignard reaction |
| 释义 |
| Name = Grignard reaction | Type = Coupling reaction | NamedAfter = Victor Grignard | Section3 = {{Reactionbox Identifiers | OrganicChemistryNamed = grignard-reaction | RSC_ontology_id = 0000014 }} The Grignard reaction (pronounced {{IPA|/ɡriɲar/}}) is an organometallic chemical reaction in which alkyl, vinyl, or aryl-magnesium halides (Grignard reagent) add to a carbonyl group in an aldehyde or ketone.[1][2] This reaction is important for the formation of carbon–carbon bonds.[3][4] The reaction of an organic halide with magnesium is not a Grignard reaction, but provides a Grignard reagent.[5] Grignard reactions and reagents were discovered by and are named after the French chemist François Auguste Victor Grignard (University of Nancy, France), who published it in 1900 and was awarded the 1912 Nobel Prize in Chemistry for this work.[6] Reaction mechanismThe carbon attached to magnesium functions as a nucleophile, attacking the electrophilic carbon atom that is present within the polar bond of a carbonyl group. The addition of the Grignard reagent to the carbonyl typically proceeds through a six-membered ring transition state.[7] See also{{Commons category|Grignard reactions}}
References1. ^{{March6th}} {{organometallics}}{{Authority control}}2. ^Chapter 19: Carboxylic Acids. Organic Chemistry 4e Carey. mhhe.com 3. ^{{cite journal|last = Shirley|first = D. A.|year = 1954|title = The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium|journal = Org. React.|volume = 8|pages = 28–58}} 4. ^{{cite book|last = Huryn|first = D. M.|year = 1991|title = Comprehensive Organic Synthesis, Volume 1: Additions to C—X π-Bonds, Part 1|pages = 49–75|chapter = Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions|editor1-last = Trost|editor1-first = B. M.|editor2-last = Fleming|editor2-first = I.|isbn = 978-0-08-052349-1|editor1-link = Barry Trost|editor2-link = Ian Fleming (chemist)|publisher = Elsevier Science|doi = 10.1016/B978-0-08-052349-1.00002-0}} 5. ^{{GoldBookRef |title=Grignard reagents |file=G02699 }} 6. ^{{cite journal| author = Grignard, V.| title = Sur quelques nouvelles combinaisons organométaliques du magnésium et leur application à des synthèses d'alcools et d'hydrocabures | journal = Compt. Rend. | year =1900| volume = 130| pages = 1322–25| url = http://gallica.bnf.fr/ark:/12148/bpt6k3086n/f1322.table}} 7. ^{{cite journal| last1 = Maruyama | first1 = K. | last2 = Katagiri | first2 = T. | year = 1989 | journal = J. Phys. Org. Chem. | doi = 10.1002/poc.610020303 | title = Mechanism of the Grignard reaction | volume = 2 | pages = 205–213 | issue = 3}} 5 : Organometallic chemistry|Carbon-carbon bond forming reactions|Magnesium|Chemical tests|Name reactions |
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