Found inside – Page xiv385 6.2 Addition Reactions of Alkynes Involving Electrophiles . ... of Organocopper Reagents to α, β-Unsaturated Carbonyl compounds–Gilman Reagents . This unique book covers fundamentals of organolithium compounds and gives a comprehensive overview of the latest synthetic advances and developments in the field. Found inside – Page 1060LiX) RCuRLi An organohalide An organolithium Gilman reagent TABLE 23.2 PREVIOUSLY SEEN REACTIONS INVOLVING LITHIUM DIALKYL CUPRATES REACTION CHAPTER ... Found inside – Page 415The syn-diastereoselectivity was obtained irrespective of the reagents type in ... has been found to react with cyano-Gilman reagents R2CuLi · LiCN (R = Me, ... Found inside – Page I-2Acid chloride(s)—cont'd reaction with alcohols, 831 reaction with amines, ... reaction with Gilman reagents, 833–834 reaction with Grignard reagents, ... Despite their widespread use in synthetic organic chemistry, the reaction pathways of organocuprate reagents are not well understood. Found insideThey react readily with acid chlorides, but do not react with aldehydes, ketones, ... Gilman reagents also undergo coupling reactions with alkyl halides. Found inside – Page iWhat are the current industrial research problems and how can they be resolved in an industrial setting? This book highlights key methods that have real impact in drug discovery and facilitate delivery of drug molecules. Found inside – Page 181As PBuz stabilized alkylcopper reagents , 11a , 11b Grignard reagents ( in ... 11e and cuprates ( Gilman reagents ) 1ld participate in analogous reactions ... This manual, edited by Norbert Krause, answers such questions, since it contains all the useful tips and tricks on organocopper compounds - information gained from personal experience by the international team of authors. Found inside – Page 592... 7, 13 Gilman cuprates 1,2-additions, 1, 107 reactions with ketones comparison with aldehydes, 1, 116 Gilman reagents conjugate additions N-enoylsultams, ... Found inside – Page 75The Gilman reagent reacts with alkyl halide to give an alkane, ... halides (Grignard reagent) in an aldehyde or ketone are added to a carbonyl ring. Found inside – Page 560In Section 18.2.1, alkyne anions react with aldehydes and ketones. 3. ... Organocuprates with this structure are sometimes called Gilman reagents, ... Found inside – Page 339C-C bond forming reactions are indicated by a box surrounding the reaction ... Mild acid (R)2 CuLi - Grignard reagent - Gilman reagent - Carbon acts as a ... Found insideCuBr-DMS has also been shown to dramatically favor 1,6-addition of Grignard reagents. Tandem organocuprate B-addition to a,B-unsaturated carbonyl compounds ... Found inside – Page 850Reactions, Principles, and Techniques Stéphane Caron ... 821 gem-Dihalides from aldehydes and ketones, 86 Gilman reagent, 25 Gold-Jacobs quinolone synthesis ... Found inside – Page 324... D. ORGANOCUPARATES - GILMAN REAGENTS Dimethyl cuparate are useful reagents ... reactions - with alkyl halides and a , B - unsaturated carbonyl compounds ... Found inside – Page 120... for CA of organocuprates to α,β-unsaturated carbonyl compounds organocuprate ... a carbocupration reaction affording compound 71 that upon rearrangement ... Found inside – Page 156... the C–C bond formation reactions have played a key role in expanding our ... as Grignard and Gilman reagents in carbonyl addition reactions) which are ... This book reflects the increasing interest among the chemical synthetic community in the area of asymmetric copper-catalyzed reactions, and introduces readers to the latest, most significant developments in the field. Found inside – Page 795Acid chlorides react readily with lithium diorganocopper (Gilman) reagents (Section 15.2) to ... they do not react with aldehydes, ketones, esters, amides, ... Found inside – Page 571In this reaction, one of the alkyl groups of the Gilman reagent replaces a halogen ... carbonyl compounds in Chapter 21, we will find that Gilman reagents ... Found inside – Page 63Gilman reagents are used to form new Carbon - Carbon bonds by reaction with Alkyl ... Primarily , Grignard reagents are used for reaction with carbonyl ... Found inside – Page 75Thus, reaction of 11 with vinyl Gilman reagent in ether at -200 gave a 94% yield of 16 as the major product, together with only a minor amount of the ... Found inside – Page 1147HCl |Reduces carbonyl compound into RCOCH, -> RCH,CH, alkane (Clemmensen ... (O)- CHs —- (O)- CH,Br 12 Gilman reagent R,Culi Reacts with acid chloride or ... Found inside – Page 221... 537 – Eschenmoser–Tanabe reaction 43-537–539 F Favorskii rearrangement ... 684, 687 Gilman reagent – Cyano-Gilman reagent 44-101, 246 – Gilman cuprate ... Found inside – Page 2264... 0277 gerade orbital, 0005 Gilman reagents, 0600 Gilman reagents, also see organocuprates Girard's reagents P and T, and hydrazones, 1285 Glaser reaction ... Found inside – Page 95421.6E Gilman reagent-Mediated couplings In addition to the Sonogashira reaction, there is another copper-based process that can couple two different ... Found inside – Page 198CuBr·DMS has also been shown to dramatically favor 1,6-addition of Grignard reagents. Tandem organocuprate β-addition to α,β-unsaturated carbonyl ... Found inside – Page 580By and large, the role and power of Grignard reagent is the reducing character of aldehydes or ketones into alcohols like hydride-reducing agents. Gilman ... Found inside – Page 314alcohols beyond the aldehyde state to give carboxylic acids. The Jones reagent reacts with secondary alcohols to give ketones, which are not further ... This book provides an introduction to the chemistry of conjugate reactions, a group of reactions that constitute one of the most important classes of chemical reactions in organic synthesis. Found insideThe expansion of synthetic methodology employing organometallic reagents and metallo-species in the lasttwenty years has been phenomenal.Two major important roles which organometallic reagents play are:Providing a means of activating small ... Found inside – Page 140Such evidence clearly indicates that all three reactants — chlorosilane , copper reagent , and substrate — cooperate in ... MezSiCl also accelerates 1,2 - addition reactions of Gilman reagents to aldehydes and changes the stereoselectivity of ... Found inside – Page 9In 1936 , he was the first to study organocuprates , organic compounds in ... reaction of an organic carbonyl , such as an aldehyde or ketone , with an ... Found inside – Page 351... these aziridines underwent anti-SN2 substitution in organocopper-mediated reactions. Whereas higher-order cuprates or Gilman reagents only resulted in ... Found inside – Page 75Many other useful reactions with other transition metals have been developed ... to as a Gilman reagent, is most conveniently prepared by reaction of two ... Found inside – Page 49915.3b ORGANOCUPRATES REACT As NUCLEOPHILES IN SUBSTITUTION REACTIONS In general , organocuprates do not react with carbon dioxide or other carbonyl ... Copper in organic synthesis has seen a tremendous development over the past ten years. This text represents the most comprehensive survey on the use of Copper and Cuprates in organic synthesis. Found inside – Page 331The use of α-bromoacetate carbanion as the cyclopropanation reagent exhibited ... addition of lithium organocuprates to a polyconjugated carbonyl compound, ... Found inside – Page 1441Hajos diketone, 0882 half-chair transition state, 0060 half-reactions, ... 1186 with organocuprates, 0718 with organolithium reagents, 0683 halides, ... Found inside – Page 343Lower yields are obtained if the enolate is produced by reaction of a silyl enol ... of Grignard reagents or Gilman reagents to α,β-unsaturated carbonyl ... Found inside – Page 97An Advanced Treatise Henry Gilman. reagents to ketones and aldehydes is normally such a rapid reaction as to preclude studies of its kinetics . Studies of the mechanism of this reaction have been based largely upon an investigation of the ... Found inside – Page 287Favoured by unreactive carbonyl groups that are less electrophilic, such as esters, ... The most common organocopper reagent is known as Gilman reagent, ... The Patai Series publishes comprehensive reviews on all aspects of specific functional groups. The book builds in a logical way from chemical bonding to resulting molecular structures, to the corresponding physical, chemical and biological properties of those molecules. Found inside – Page 75Many other useful reactions with other transition metals have been developed ... to as a Gilman reagent , is most conveniently prepared by reaction of two ... Found inside – Page 836The reaction proceeds via radical anion 205 as shown in Scheme 7.34. Exposure of aromatic Gilman reagent drofuran solvent Me provides 2 bis(enones) 207∘ C ... Found inside – Page 2-22(c) reaction with carboxylic acid derivatives Carboxylic acid derivatives like ... organocuprates or gIlman reagents New carbon—carbon bond can be formed by ... Found insideOrganometallics except Gilman reagents readily react with hydrogen atoms ... 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