Iodo-Gilman reagents Me 2 -CuLi´LiI, Bu 2 CuLi´LiI, and BuThCuLi´LiI and cyano-Gilman reagents (ne  e ªhigher order cyanocupratesº Me 2 CuLi´LiCN, Bu 2 CuLi´LiCN, and BuThCuLi´LiCN react with 2-cyclohexenone at various rates, which depend upon the R groups (Me, Bu, Th thienyl), Li salt (LiI vs. LiCN), solvent (ether vs. THF), and amount of trimethylsilyl chloride (TMSCl) additive. The effect of the Li salt (CuI vs. CuCN precursor) is less than that of solvent or TMSCl. The butylcuprate-iodocyclohexane reaction has also been examined as a function of Li salt, solvent, and TMSCl additive, and similar effects are observed. The reactivity matrix R with elements r i,j is a convenient way to store and present a large amount of relative reactivity data. Entry r i,j is the ratio of the rate with reagent i to the rate with reagent j, which we approximate by using yields measured after a short time (4 s). The logarithmic reactivity profile (LRP) provides an efficient means for determining yields under conditions where such comparisons are valid. The results of a large number of 4-point LRPs and related reactions are tabulated and analyzed to provide a clearer picture of organocuprate reactivity.

Iodo-Gilman reagents Me 2 -CuLi´LiI, Bu 2 CuLi´LiI, and BuThCu-Li´LiI and cyano-Gilman reagents (ne  e ªhigher order cyanocupratesº Me 2 Cu-Li´LiCN, Bu 2 CuLi´LiCN, and BuTh-CuLi´LiCN react with 2-cyclohexenone at various rates, which depend upon the R groups (Me, Bu, Th thienyl), Li salt (LiI vs. LiCN), solvent (ether vs. THF), and amount of trimethylsilyl chloride (TMSCl) additive. The effect of the Li salt (CuI vs. CuCN precursor) is less than that of solvent or TMSCl. The butylcuprate-iodocyclohexane reaction has also been examined as a function of Li salt, solvent, and TMSCl additive, and similar effects are observed. The reactivity matrix R with elements r i,j is a convenient way to store and present a large amount of relative reactivity data. Entry r i,j is the ratio of the rate with reagent i to the rate with reagent j, which we approximate by using yields measured after a short time (4 s). The logarithmic reactivity profile (LRP) provides an efficient means for determining yields under conditions where such comparisons are valid. The results of a large number of 4-point LRPs and related reactions are tabulated and analyzed to provide a clearer picture of organocuprate reactivity.

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A facile synthesis of pharmacologically important dibenzo [b,fl[1,4]heteroazepine based tricyclic compounds is reported. Reaction of diaryl compounds such as o-amino-diphenyl ether and o-amino-diphenyl sulfone with n-butyllithium yielded the C,A/-dilithio-diaryl species in excellent yields. These dilithio intermediates were reacted with appropriate ester moieties to synthesize tricyclic compounds based on the dibenzo[b,/][1,4]heteroazepine framework.

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