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Model studies of the Sandmeyer chlorination reaction. General conditions: HBF4 (1.3 equiv), tBuONO (1.3 equiv), solvent 1, 0 °C, 30 min; cooled to specified temperature, then treated with CuCl (50 equiv) and CuCl2 (60 equiv) in solvent 2, and warmed to room temperature over 1 h. Product ratios were determined by LC/MS analysis of the crude reaction mixture. Isolated yields are given in parentheses.
