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Phosphites were of little use, but nitrogen-containing phosphine ligands had the advantage that phosphine-containing impurities could be removed by a simplc dilute acid work-up. The active copper prepared utilizing trialkylphosphines, such as PEt3, PBu3 or P(Cy)j, gave 10-30% of homocouplcd products when using alkyl bromides (2 RBr + R-R). Higher proportions of the homocoupled product were found when using alkyl iodides. The tendency for homocoupling was highly dependent upon the ratio of copper to alkyl halide used, the tempcraturc of addition, and the manner in which the alkyl halide was added.
C) Bis-electrophiles were added to the THF solution of the diene-magnesium reagent at -78 "C. The reaction mixture was then stirrcd at -78 OC for 1 h prior to warming to the specified temperature. (A) reflux (15 h); (B) room temperature (30 min); (C) reflux (10 h); (D) room temperature (10 h); (E) -30 "C; (F) room temperature (30 h). lic enol 2,3,4,5,6,7-hexahydro-2-methyllti-inden-2-01 (4) was obtained. It was found that the initial product generated upon treating the 1,2-bis(methylene)cycloalkanemagnesium, 1, with ethyl acetate was 2, a magnesium salt of a spiroenol containing a cyclopropane ring.
B) Isolated yields. c) Yield was based on amount of active magnesium. d) A 1 : 1 mixture of diastereomers as determined by 'H NMR. 7 Synthesis of y-Lactams from Conjugated Diene-Magnesium Reagents y-Lactams are important intermediates in synthetic routes to five-membered heterocyclic compounds. 2 Rirkr Mognesium, Colciurn, Strontium, rznd Bririiinz 21 foundly important family of biologically active secondary metabolites, many of which have potential uses in medicine and agriculture 1431. Synthetic interest in this class of molecules has been intense, particularly in the past decade .