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Phenylthio cuprates

Lithium (cyelopropyl)(phenylthio) cuprate (l).27 This cuprate is prepared by addition of cyclopropyllithium to phenylthiocopper in THF at -78- — 20°. It converts /J-iodo enones (2) into /1-cyclopropyl enones (3) in excellent yield, even when 2 is substituted at the a-position by a methyl group. The products are useful because they rearrange when heated to annelated cyclopentenes (4 and/or 5). The rearrangement is particularly efficient when R = H, and results in 5 as the major product ( 85% yield). [Pg.191]

Mixed cuprates derived fiom deprotonation and transmetalation of ketone dimethylhydrazones, using copper(I) thiophenoxide as the copper(I) source, are effective as enolate equivalents in 1,4-conjugate additions to a,3-unsaturated esters. The mixed phenylthio cuprate was found to exhibit approximately the same selectivity and reactivity in these reactions as a similar homocuprate (63) prepaid from the aza-allyllithium reagents and copper(I) iodide (equation 29). [Pg.518]

Lithium n butyl (phenylthio) cuprate has been used in nucleophilic substitution reactions of arenesulfonyl fluorides, al-lylic acetates, 9 BBN, propargyllc carbamates, and bromo-alkenes, as well as in nucleophilic additions to acetoxy-epoxides. It Is a good choice for 1,4-addItIon of an n-Bu group, having been used in 1,4 addition-elimination reactions of a-oxoketene dithloacetals and 3-halo-2-cycloalkenones, and in tandem vicinal dialkylation reactions of 5-methyleneoxa-zolones and alkynes. A typical example Is the use of the reagentin the stereospecific synthesis of (, -2-heptenoicacidfrom acetylene (eq 1). ... [Pg.325]

Related Reagents. For related heterocuprates, see lithium methyl(phenylthIo)cuprate for discussion of lithium dialkyl-cuprates, see lithium dimethylcuprate. [Pg.325]

Alternate Name lithium [(a-diethoxymethy vlnyl] (phenylthio) cuprate. [Pg.327]

Related Reagents. 3,3-Diethoxy-1-propen 2 ylcopper Lithium Bis(3,3-diethoxy l-propen-2-yl)cuprate and Lithium (3,3-Diethoxy-1 -propen-2 yl) (3,3-dimethyl-1 -but5myl)cuprate for related heterocuprates, see Lithium Methyl(phenylthio) cuprate for discussion of lithium dialkylcuprates, see Lithium Dimethyl cuprate. [Pg.329]

LITHIUM 1-METHYL-2-(2-METHYL-1-( )-PROPENYL)CYCLOPROPYL(PHENYLTHIO)CUPRATE... [Pg.330]

Lithium 1 -Methyl- 2 - (2 -methyl-1 - ( -propenyl) cyclopropyl (phenylthio) -cuprate... [Pg.330]

Related Reagents. Lithium Bis(2-vinylcyclopropyl)cup-rate Lithium Dimethylcuprate Lithium Methyl (phenylthio) cuprate. [Pg.335]

Lithium l-Methyl-2-(2-methyl 1 propenyl)cyclopropyl(phenylthio)cuprate 330 University of Bristol, Bristol UK... [Pg.660]

Lithium (3,3-Diethoxy-1-propen-2 yl)(phenylthio)cuprate, 327 C13H19NO2S... [Pg.667]

See other pages where Phenylthio cuprates is mentioned: [Pg.58]    [Pg.124]    [Pg.124]    [Pg.124]    [Pg.535]    [Pg.325]    [Pg.325]    [Pg.326]    [Pg.326]    [Pg.326]    [Pg.327]    [Pg.327]    [Pg.328]    [Pg.653]    [Pg.653]    [Pg.665]    [Pg.666]   


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Additions lithium phenylthio cuprate

Additions phenylthio cuprate

Butyl(phenylthio)cuprate

Cyclopropyl(phenylthio)cuprate

Diethoxy-l-propen-2-yl)(phenylthio)cuprate

LITHIUM PHENYLTHIO CUPRATE

Lithium phenylthio cuprate conjugate additions

Lithium phenylthio cuprates

Phenylthio cuprates 1,2-addition

Phenylthio(2-vinylcyclopropyl)cuprate

Phenylthio(trimethylstannyl)cuprate

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