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Topic: Organolithium reagent

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	Organolithium reagent Summary
		Organolithiums are a type of organometallic compound in which the carbon of an organic group is directly bonded to a lithium atom.
		An organolithium reagent is an organometallic compound with a direct bond between a carbon and a lithium atom.
		Organolithium reagents are industrially prepared by the reaction of an organohalogen with lithium metal, i.e.
	www.bookrags.com /Organolithium_reagent (933 words)

	Organolithium reagent - Wikipedia, the free encyclopedia (Site not responding. Last check: 2007-10-18)
		An organolithium reagent is an organometallic compound with a direct bond between a carbon and a lithium atom.
		Organolithium reagents are industrially prepared by the reaction of an organohalogen with lithium metal, i.e.
		Organolithium compounds are strongly polarised by the electropositive character of lithium.
	en.wikipedia.org /wiki/Organolithium_reagent (573 words)

	Organolithium reagent: Encyclopedia topic (Site not responding. Last check: 2007-10-18)
		An organolithium reagent is a carbon nucleophile similar to a Grignard reagent (Grignard reagent: a grignard reagent is an alkyl- or aryl- magnesium halide....
		Preperation of Organolithium reagents is usually achieved by reaction of an organohalogen with lithium (lithium: A soft silver-white univalent element of the alkali metal group; the lightest metal known; occurs in several minerals) metal, i.e.
		Organolithium reagents are used in organic synthesis, and are known under the collective class of organometallic compounds.
	www.absoluteastronomy.com /reference/organolithium_reagent (132 words)

	Organolithium reagent - One Language (Site not responding. Last check: 2007-10-18)
		An organolithium reagent is a carbon nucleophile similar to a Grignard reagent.
		Preperation of Organolithium reagents is usually achieved by reaction of organohalogen with lithium metal, i.e.
		Organolithium reagents are used in organic and in organic synthesis, and are known under the collective class of organometallic compounds.
	www.onelang.com /encyclopedia/index.php/Organolithium_reagent (105 words)

	Organometallic Reagents
		Organolithium reagents are available commercially as solutions in inert solvents such as diethyl ether, tetrahydrofuran (THF), or pentane.
		The procedure for generating either type of reagent is similar: an alkyl or aryl halide is treated with magnesium or lithium metal in a dry, inert solvent, most commonly anhydrous ether.
		Whether an organometallic reagent is classified as a base or a nucleophile depends on whether it forms a bond with a hydrogen atom or a carbon atom.
	www.biologie.uni-hamburg.de /b-online/library/newton/Chy251_253/Lectures/Organometallic_Reagents/OrganometallicsFS.html (885 words)

	Nucleophile: Encyclopedia topic (Site not responding. Last check: 2007-10-18)
		In chemistry (chemistry: The science of matter; the branch of the natural sciences dealing with the composition of substances and their properties and reactions), a nucleophile (literally nucleus lover) is a reagent (reagent: A chemical agent for use in chemical reactions) which is attracted to centres of positive charge.
		Grignard reagent (Grignard reagent: a grignard reagent is an alkyl- or aryl- magnesium halide....
		Organolithium reagent (Organolithium reagent: an organolithium reagent is a carbon nucleophile similar to a grignard reagent....
	www.absoluteastronomy.com /reference/nucleophile (524 words)

	Martin Mickoleit, Ute Bäumer, Kathleen Schmohl, Rhett Kempe, Hartmut Oehme: The Synthesis, Structure and Reactivity of ...
		Treatment of dichloromethyl-tris(trimethylsilyl)silane (1) with organolithium compounds leads to the formation of bis(trimethylsilyl)silanes 2.
		This process, which will be discussed in detail, involves transient silenes as intermediates, which are trapped by excess organolithium reagent to give 2 as the final products [1].
		When organolithium derivatives are used in this reaction, bearing substituents R which due to their bulkiness or by intramolecular donor acceptor interactions provide a sufficient stabilization to the Si=C system, the reaction can be stopped at that stage and indefinitely stable silenes can be isolated and characterized.
	wwwswt.informatik.uni-rostock.de /englisch/projekte/NM_Uni/Archive/Oehme2a.html (333 words)

	Physical Organic Chemistry - Organic Chemistry - Department of Chemistry (Site not responding. Last check: 2007-10-18)
		The reactivity of organolithium compounds is known to be affected by aggregation and solvation.
		The possibility of using organolithium compounds in asymmetric synthesis is very appealing, however, to control the reactivity and selectivity it is necessary to identify the structure(s) of the reacting complex.
		The second approach is to use an organolithium reagent that is chiral in itself, for example the use of a chiral lithium amide.
	www.chem.umu.se /dep/orgchem/forskning/physorganic/Organolithium/fobakgr.stm (1261 words)

	METHYL KETONES FROM CARBOXYLIC ACIDS: CYCLOHEXYL METHYL KETONE
		in which the lithium reagent is titrated with sec-butyl alcohol, utilizing the charge transfer complex formed from bipyridyl or o-phenanthroline and the lithium reagent as an indicator.
		During this procedure it is not uncommon for the lithium carboxylate to separate during the addition of the first mole of organolithium reagent and then to react and redissolve as the second equivalent of organolithium reagent is added.
		In all cases it is important not to add a large excess of organolithium reagent and to add the final reaction mixture to the aqueous quenching bath slowly and with vigorous stirring if the formation of substantial amounts of alcohol by-product is to be avoided.
	www.orgsyn.org /orgsyn/orgsyn/prepContent.asp?prep=cv5p0775 (1190 words)

	United States Patent Application: 0030130511
		The process as claimed in claim 5, wherein the exchange reagent is an exchange reagent as claimed in claim 1, the magnesium compound represented by the formula (I) as described in claim 1 is n-butylmagnesium bromide or n-butylmagnesium choride, and the organolithium compound represented by the formula (II) is n-butyllithium.
		The process as claimed in claim 5, wherein the exchange reagent is an exchange reagent as described in claim 2, the compound represented by the formula (III) as described in claim 2 is tri-n-butylmagnesium lithium, and the compound represented by the formula (IV) is tetra-n-butylmagnesium dilithium.
		As a reagent employed in the halogen-metal exchange reaction are exemplified Grignard reagents and organolithium reagents.
	appft1.uspto.gov /netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=/netahtml/PTO/srchnum.html&r=1&f=G&l=50&s1="20030130511".PGNR.&OS=DN/20030130511&RS=DN/20030130511 (8879 words)

	Synthesis of Alcohols (Site not responding. Last check: 2007-10-18)
		Organometallic reagents are organic compounds that are bonded to a metal.
		OrganoMagnesium reagents are prepared by reacting an alkyl halide with metallic Magnesium using anhydrous diethyl ether as the solvent.
		OrganoLithiums may be prepared with any alkyl halide but alkyl iodides, R-I, are most reactive and alkyl flourides the least reactive and generally not used in preparing the Organometallic reagent.
	members.aol.com /logan20/alc_syn.html (1717 words)

	Grignard Reaction (Site not responding. Last check: 2007-10-18)
		A Grignard reagent is an example of organomettalic reagents, which are valuable synthetic tools in organic chemistry.
		The resulting reagent, "RMgX" is a very polar reagent and a very strong Lewis base and therefore will be easily protonated by water, which acts as a strong acid in contact with a Grignard reagent.
		A carboxylic acid was synthesized by the addition of dry ice (CO) to the reagent and subsequent protonation of the adduct.
	www.chemistry.emory.edu /mccormick/reports/grignard.htm (1094 words)

	Media Portfolio
		Organolithium reagents can be used to synthesize ketones from carboxylic acids.
		Organolithiums are so reactive toward carbonyls that they attack the lithium salts of carboxylate anions to give dianions.
		To stop at the ketone stage, a weaker organometallic reagent is needed: one that reacts faster with acid chlorides than with ketones.
	wps.prenhall.com /wps/media/objects/340/348272/wade_ch18.html (2075 words)

	[No title] (Site not responding. Last check: 2007-10-18)
		The present invention is directed to a novel process for preparing heteroaryl and unsaturated heterocycloalkylmagnesium reagents that are useful in the synthesis of a variety of pharmaceuticals, in particular certain cysteine protease inhibitors.
		Heteroaryl and unsaturated heterocycloalkylmagnesium reagents are useful in the synthesis of a variety of pharmaceuticals, such as renin inhibitors and cysteine protease inhibitors.
		The heteroarylmagesium reagent used in this process is prepared by first treating a heteroaryl with an organolithium reagent and then converting the resulting lithiated species into a Grignard reagent under transmetallation reaction conditions.
	www.wipo.int /cgi-pct/guest/getbykey5?KEY=03/87068.031023&ELEMENT_SET=DECL (4494 words)

	Process for producing keto nitrile derivative - Patent 5688985
		In addition to these Grignard reagents, organomagnesium compounds represented by formula (X): ##STR11## (wherein R.sub.7 and R.sub.8, which may be the same or different, each represent a lower alkyl group, a benzyl group or a phenyl group, or they may be taken together to form a 5- or 6-membered ring), can also be used.
		Organolithium reagents which can be used as a carbanion generator in the present reaction include vinyl lithium, propyl lithium, N-isopropylaminolithium, N,N-diphenylaminolithium, N-methyl-N-phenylaminolithium and N-t-butylaminolithium.
		In the case of using the organolithium reagent as a carbanion generator, suitable reaction solvents include hydrocarbons such as toluene and heptane, ether solvents such as those used for the above-described organomagnesium reagents, and hydrocarbon/ether mixed solvents.
	www.freepatentsonline.com /5688985.html (2760 words)

	AROMATIC HYDROCARBONS FROM AROMATIC KETONES AND ALDEHYDES: 1,1-DIPHENYLETHANE
		The organolithium reagent was generated in situ in ether from 1-bromobutane.
		The organolithium reagent was generated in situ in ether from bromobenzene.
		Commercial organolithium reagents such as n-butyllithium in hexane or phenyllithium in cyclohexane–ether were satisfactory when twice as much lithium is used for the reduction step.
	www.orgsyn.org /orgsyn/orgsyn/prepContent.asp?rxntypeid=20&prep=CV6P0537 (922 words)

	Diastereocontrolled synthesis of 2-amino alcohols - Patent 4743694
		The addition of organolithium to dimethylhydrazones of certain ethers of a-hydroxyaldehydes results in the synthesis of threo- or erythro- intermediates readily convertible to threo- or erythro-2-amino alcohols.
		The key step of the process is the diastereoselective addition of an organolithium reagent across the double-bond of an aldehyde dialkylhydrazone, the starting material having in place an ether of an a-hydroxy group thereof.
		After quenching the excess organolithium reagent by addition of sufficient water the reaction is worked up by standard purification procedures.
	www.freepatentsonline.com /4743694.html (1788 words)

	Grignard Experiment
		The Grignard reaction is typical of a large class of "Organometallic" reactions in that the Grignard reagent acts as a source of nucleophilic carbon which forms a new carbon-carbon bond by attacking a relatively electron deficient or electropositive carbon of a second reactant.
		Typically this second substance is an aldehyde, ketone or organic ester, but the very reactive Grignard reagent will attack any of a large variety of acidic or electropositive reagents.
		In this sense the organometallic reagents like the Grignard reagent or the Organolithium reagent are similar to any other nucleophilic substances.
	www.sonoma.edu /users/t/trowbrda/336/grignard.html (1005 words)

	Homework 2Answer Key
		represents one combination of an organolithium reagent and a ketone that may be used to prepare
		Questions 4-6 involve a retrosynthetic analysis of the synthesis of 4-penten-2-one by a sequence of reactions which includes the preparation and reaction of an organometallic reagent.
		Note that the carbanionic center of the original organolithium reagent is conjugated to the adjacent double bond
	www.usm.maine.edu /~newton/Chy251_253/Homeworks/Chy25301/H02/H02Key (618 words)

	Titration of Organolithium Reagents: Handling Air and Moisture Sensitive Compounds in an Organic Experiment
		Described herein is an organic experiment involving the titration of organolithium reagents, which are air- and moisture-sensitive.
		Upon synthesis and characterization, this compound is conveniently applied both as the titration standard and color indicator in the titration of an organolithium reagent.
		This experiment is pedagogically valuable because it revisits the fundamental concepts and techniques in a titration, but also features advanced topics involving the structures and reactivities of organolithium reagents.
	chemeducator.org /bibs/0010005/1050353sl.htm (213 words)

	Steffen Runge, PhDThesis, FU Berlin
		The meso-alkylsubstituted 2-formylporphyrins were used for a detailed study on their reactivity with organolithium reagents.
		Depending on the organolithium reagent used various olefinic porphyrins are accessible, provided the stability of the intermediary carbenium ion is high enough.
		Using appropriate reagents one-pot reactions can be performed that achieve a coupling reaction, dehydrogenation with hydride shift and demetalation of porphyrins.
	www.diss.fu-berlin.de /2000/39/indexe.html (316 words)

	ChemActivity 36 SDE Part B (Site not responding. Last check: 2007-10-18)
		For the reaction in Model 3, the organolithium reagent is added and allowed to react BEFORE dilute acid is added.
		Predict what side-products would form if these two reagents were added at the same time.
		Show the mechanism of the imine formation reaction when an aldehyde is treated with an amine with an acid catalyst.
	home.earthlink.net /~cuachemistry/organic/SDEAns/AnsSDE36B.htm (148 words)

	[No title] (Site not responding. Last check: 2007-10-18)
		The present process therefore comprises the steps of lithiating a suitable starting compound, such as ortho-bromothioanisole or ortho- bromoanisole, then changing the organolithium reagent of the starting compound into an organometal halide reagent which is then reacted with an appropriate halophosphine producing the desired product.
		Useful lithium reagents include elemental lithium and organolithium compounds, such as n-butyllithium, isobutyl- lithium and phenyllithium.
		The reaction between the substituted haloaryl and the lithiating reagent is preferably carried out in a non-polar solvent, such as an aliphatic ether, e.
	www.wipo.int /cgi-pct/guest/getbykey5?KEY=00/02890.000120&ELEMENT_SET=DECL (6723 words)

	cite.htm
		For example, according to the journal article "rapid metal-halogen exchange induced by treating allenic iodides with tert-BuLi was not usually complicated by direct metalation of the allene function".
		They used it in citation as a sample of an organolithium reagent reacting with a double bond, and were doing further research to find a similar reagent more tolerant to functional groups.
		This journal was also researching the preperation of an organolithium reagent that would further be used in a substution reaction.
	www.umich.edu /~chemh215/W01HTML/SSG4/ssg2/misc/cite.htm (274 words)

	[No title]
		"Substitution of a Bridgehead Bromide by Primary Organolithium Reagents." Michael Harmata and Sumrit Wacharasindhu.
		"Substitution of a Bridgehead Bromide by Primary Organolithium Reagents." Michael Harmata and Sumrit.
		"The Preparation of a Bridgehead Organolithium Reagent." Michael Harmata and Patrick Kirchhoefer.
	www.chem.missouri.edu /harmata/presentations.html (4517 words)

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