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Addition times varied between 8 and 16 h. Changing the substrate required reoptimization of addition times. Alkylidene malonate 10i proved resilient to this protocol, affording only 55% conversion under the optimized addition time of 16 h. We suggest that the bulk of this substrate is responsible. From this and other data, we concluded that slow addition would prove insufficient as a general solution.
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Geometry optimizations were performed at the PM3(tm) level using the Spartan Semiempirical Program 5.0 (Wavefunction Inc., Irvine, CA 92612) on a Silicon Graphics Impact 10000 (195 MHz, 128 M RAM) running IRIX 6.2. Calculations were performed without counterions or solvent using the following parameters: optcycle = 5000, maxcycle = 10000, charge = 2, multiplicity = 2. Calculations converged (energy difference between cycles <0.0005 kcal/mol) in ≤ 4 h CPU time.
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This is not suprising considering that this ring needs to accommodate five 120° angles (C-C-O, C-C-C, and C-O-Cu), one 90° angle (square planar Cu), and two long bonds (2.0 Å, Cu-O). Indeed, a molecular mechanics geometry optimization of this ring alone predicts an identical conformation despite the failure of PM3 to do likewise.
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