The McMurry reaction is an organic reaction in which two ketone or aldehyde groups are coupled to form an alkene using a titanium chloride compound such as titanium(III) chloride and a reducing agent. The reaction is named after its co-discoverer, John E. McMurry. The McMurry reaction originally involved the use of a mixture TiCl3 and LiAlH4, which produces the active reagents. Related species have been developed involving the combination of TiCl3 or TiCl4 with various other reducing agents, including potassium, zinc, and magnesium.[1][2] This reaction is related to the Pinacol coupling reaction which also proceeds by reductive coupling of carbonyl compounds.
^Richards, Ian C. (2001). "Titanium(IV) Chloride-Zinc". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt125. ISBN 0471936235.
^Banwell, Martin G. (2001). "Titanium(III) Chloride-Lithium Aluminum Hydride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt129. ISBN 0471936235.
Edition. 25 (3): 257. doi:10.1002/anie.198602571. McMurryreaction in organic-chemistry.org Mcmurryreaction at the University of Sussex[permanent dead link]...
a cycloalkene. When two carbonyl groups are coupled and undergo a McMurryreaction, there is a possibility of the formation of cycloalkenes under specific...
the McMurryreaction Lillian McMurry (1921–1999), American record producer McMurray (disambiguation) McMurry University in Abilene, Texas The McMurry reaction...
coupling can be followed up by a pinacol rearrangement. A related reaction is the McMurryreaction, which uses titanium(III) chloride or titanium(IV) chloride...
removed by the reductive coupling of ketones, as illustrated by the McMurryreaction. Epoxides can be deoxygenated using the oxophilic reagent produced...
Such conversions are sometimes valuable in organic synthesis. In the McMurryreaction, ketones are converted into alkenes using oxophilic reagents: 2 R2CO...
these olefination reactions often lead to the formation of diols—the McMurryreaction—rather than the methylenation or alkylidenation of aldehydes. To circumvent...
reduction (the McMurryreaction). If different ketones are to be coupled, a more complicated method is required, such as the Barton–Kellogg reaction. A single...
Lillian Shedd McMurry (December 30, 1921 – March 18, 1999) was one of the earliest American female record producers and owner of Trumpet Records. She...
doi:10.1021/ja01646a008. Michel Ephritikhine (1998). "A new look at the McMurryreaction". Chem. Commun. (23): 2549–2554. doi:10.1039/a804394i. Elschenbroich...
In organic chemistry, the Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane (R−NO2) to...
In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael...
3 was obtained via an SN2 reaction involving a mesylate derived from acetal 4.9. Ring B was closed via a McMurryreaction involving dialdehyde 4.8 which...
from Ancient Greek hydro- 'water', and lysis 'to unbind') is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term...
after reflux with 1,4-dioxane. This is what is now known as the McMurryreaction - McMurry published a year later and cited both Mukaiyama and the group...
Synthesis of (Z)-4-Hydroxytamoxifen and (Z)-4-Hydroxytoremifene via McMurryReaction". The Journal of Organic Chemistry. 61 (11): 3890–3893. doi:10.1021/jo952279l...
1039/JR9520001127. Ho, Tse-Lok (1992). Tandem organic reactions. New York: Wiley. ISBN 978-0-471-57022-6. McMurry, John (2008). Organic chemistry (7th ed.). Belmont...
The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst...
the alkylated ketone. In the Corey-Enders reaction, a hydrazone replaces the amine for enantioselection. McMurry, John (21 March 2003). Organic Chemistry...
The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as...
series Isotope electrochemistry List of battery types Sacrificial anode McMurry, John; Fay, Robert C.; Robinson, Jill K. (2015). Chemistry (7th ed.). Boston:...
retained IUPAC names Link Archived 9 July 2023 at the Wayback Machine McMurry, John E. (1992), Organic Chemistry (3rd ed.), Belmont: Wadsworth, ISBN 0-534-16218-5...
In organic chemistry, the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene (R2C=CR2) into a neutral alcohol. In...
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