Lithium phenylthio cuprates

SECONDARY AND TERTIARY ALKYL KETONES FROM CARBOXYLIC ACID CHLORIDES AND LITHIUM PHENYLTHIO(ALKYL)CUPRATE REAGENTS tert-BUTYL PHENYL KETONE... [Pg.122]

For use of other organocopper reagents in converting carboxylic acid chlorides to ketones, see G. H. Posner and C. E. Whitten, Tetrahedron Lett., 1815 (1973) G. H. Posner, C. E. Whitten, and P. E. McFarland, J. Amer. Chem. Soc., 94, 5106 (1972). For a recent report on direct and convenient preparation of lithium phenylthio (alkyl)-cuprate reagents, see G H Posner, D J Brunelle, and L. Sinoway, Synthesis, 662 (1974). [Pg.127]

Lithium, methyl, 55,7, 10 Lithium, phenyl-, 55,11 Lithium phenylthio(alkyl)cuprates, 55,122 LITHIUM, phenyltluo(fe/f-butyl)cuprate [Lithium, phenylthio( 1,1 -dimethyl-ethyl)cupiate, 55,122 Lithium, 1-propenyl-, 55, 111 LITHIUM, ( >l-propenyl-, 55, 103 Lithium thiophenoxide [Ben7enethiol, lithium salt], 55, 122... [Pg.142]

Interesting and useful variations in R involve more complex alkyllithium reagents. For example, the treatment of (3-iodoenone (10) with lithium phenylthio(2-vinylcyclopropyl)cuprate gave the conjugate addition product (11) as an intermediate en route to the bicyclic dienone (12 82% equation 9).35 The ability of a cuprate to deliver a functionalized group to the enone was a definite advantage in this synthetic scheme. [Pg.173]

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]

Lithium naphthalenide, 284-285 Lithium phenylthio(trimethylstannyl)-cuprate, 330 Lithium phthalide, 285 Lithium 2,2,6,6-tetramethylpiperidide, 145, 281,285-286, 362 Lithium trialkylborohydrides, 278 Lithium triethylborohydride, 286 Lithium tricthylborohydride-Aluminum t-butoxide, 287 Lycorine, 503... [Pg.298]

When enantiopure (+)-(/ )-5-methyl-2-cyclohexenone is treated with lithium phenylthio(tri-methylstannyl)cuprate followed by iodomethane in hexamethylphosphoric triamide, a single product is obtained with [a]n8 +134 (CH,OH)16. [Pg.1255]

Lithium naphthalenide, 247 Lithium phenylethynolate, 247-248 Lithium phenylthio( trimethylstannyl)-cuprate, 289... [Pg.263]

The use of the mixed lithium phenylthio(alkyl)cuprates, PhSCuRLi, for conjugate addition to a,p-un-saturated carbonyl compounds is well known. - The reaction of phenylthiocuprates derived from Grignard reagents with cinnamates and crotonates has also been reported (Scheme 50). ... [Pg.121]

Lithium methylsulfinylmethylide, 342 Lithium methyl(vinyl)cuprate, 342-343 Lithium naphthalenide, 415 Lithium organocuprates, 225 Lithium perchlorate, 103 Lithium phenylethynolate, 343 Lithium phenylthio(alkyl)cuprates, 344, 465... [Pg.377]

Lithium phenylthio[(a-diethoxymethyl)vinyl] cuprate, (I). Mol. wt. 308.84. Preparation ... [Pg.110]

CONJUGATE ADDITION Diethyl acetylmethylmalonate. Dilithium trimethyl cuprate. N,N-Dimethylbenzeneselenenamide. Dimethyl sulfoxide. Lithium di-(2-vinylcyclo-propyl)cuprate. Lithium phenylthio(cyclopropyi)cuprate. Lithium phenylthio[(a-diethoxymethyl)vinyi]cuprate. 2-(2-Mcthoxy)-aIiylidene-l,3-dithiane. 2-Nitropropene. Tetra- -butylammonium fluoride. Titanium(IV) chloride -is(methyithio)methyl-lithium. [Pg.220]

CYCLOPENTANE ANNELATION Lithium phenylthio(cyclopropyl)cuprate. [Pg.220]

Lithium phenylthio [ (a-diethoxymethyl)-vinyl] cuprate, 212-213 Lithium phenylthio(2-vinylcyclopropyl)-... [Pg.243]

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