PhTD disappeared immediately after each drop was added. Hexane (100 mL) was then added to precipitate the product, and the precipitate was filtered through a sintered glass funnel to give 0.680 g of 9 was identified by NMR. The filtrate was concentrated to give 3.800 g of p-tert-butylstyrene as determined by NMR. No evidence for the presence of a 1:1 DA adduct was obtained.MeTD (0.500 g, 4.42 mmol) in 10 mL of methylene chloride and p-tert-butylstyrene (7.080 g, 44.2 mmol) in 20 mL of methylene chloride were shown, by a similar procedure, to give 0.700 g of 10 and essentially quantitative recovery of unreacted ptert-butylstyrene. No evidence for a 1:1 DA adduct was obtained.Reaction of PhTD/MeTD with ptert -Butylstyrene (-78 °C; 1:1 Molar Ratio). PhTD (0.500 g, 2.88 mmol) in 20 mL of methylene chloride was added to p-tert-butylstyrene (4.572 g, 28.8 mmol) in 20 mL of methylene chloride with vigorous stirring and cooling with dry ice-isopropyl alcohol (-78 °C). The characteristic red color of PhTD disappeared immediately. The resultant solution was concentrated, and hexane (100 mL) was added to precipitate the product, which, after filtering and drying, gave 0.725 g of 9. The filtrate was concentrated to give 4.238 g of p-tert-butylstyrene as determined by NMR. The reaction between MeTD (0.250 g, 2.21 mmol) and ptert-butylstyrene (3.548 g, 22.1 mmol) was similarly carried out and gave 0.386 g of 10 and 3.370 g of p-tert-butylstyrene. No evidence for a 1:1 adduct was obtained in either experiment.Reaction of PhTD with p-tert-Butylstyrene (-78 °C; 1:10 Molar Ratio) at High Dilution. PhTD (0.500 g, 2.88 mmol) in 150 mL of methylene chloride was added dropwise from a dropping funnel to a solution of p-tert-butylstyrene (4.572 g, 28.8
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