Lithium tetrachlorocuprate

A second nonselective synthesis involved chain extension of the tosylate of ( )-citronellol (82) with 2-methylpentyl magnesium bromide and lithium tetrachlorocuprate catalysis to give the carbon skeleton 83 (Scheme 12A) [92]. Allylic oxidation with Se02 and ferf-butylhydroperoxide, hydrogenation of the... 

The stereoselective synthesis of (Z,Z)-3,13-octadecadienyl acetate (15), the sex attractant of the smaller clear wing moth, Synanthedon tenuis, was performed by Uchida et al. (1979) according to Scheme 1.31. The key step of this synthesis is the coupling of the Grignard reagent 16 with the intermediate 17 in the presence of lithium tetrachlorocuprate, as described by Fouquet and Schlosser (1974). 

Dilithium tetrachlorocuprate is recommended as an additive for cross coupling of Grignard compounds with tosylates even allylic and benzylic acetates give good yields . a-Methylene-ketones, -carboxylic acids and -lactones have been prepared via sulfides and sulfoxides. A convenient and general synthesis of acetylene derivatives from boranes via the reaction of iodine with lithium 1-alkynyltriorganoborates has been published ar-Nitrostyrenes can be easily obtained by a Wittig synthesis with formaldehyde in an aqueous medium . A new synthesis of unsym. ketones by reaction of dialkyldiloroboranes with lithium aldimines has recently been published . Metallo aldimines have also served for the synthesis of a variety of other compound classes such as a-hydroxyketones, a-keto acids, nitriles, and for the asym. synthesis of a-amino acids . Polycondensations of malononitriles with benzylic chlorides have been carried out quantitatively under mild conditions in dimethyl sulfoxide with triethylamine as acid acceptor . Carbonyl compounds can react with dibromoacetonitrile to yield a-bromo esters with additional carbon atom . ... 

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