By Prof. L. Brandsma, Prof. H. D. Verkruijsse, Prof. S. F. Vasilevsky (auth.)
Homogeneous catalysis is a crucial procedure for the synthesis of high-valued chemical compounds. L. Brandsma has conscientiously chosen and checked the experimental strategies illustrating the catalytic use of copper, nickel, and palladium compounds in natural synthesis. All techniques are on a preparative scale, make fiscal use of solvents and catalysts, stay away from poisonous elements and feature excessive yields.
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3 mol (21 g, a large excess) of freshly distilled ethyl vinyl ether was added over 5 min. The solution was stirred for 10 min at -80°C, after which the temperature was allowed to rise over 15 min to -40 0c. 5 g) was added over 5 min at -60 to -70°C, after which the cooling bath was removed and the temperature allowed to rise to 0 0c. Water (100 ml) was added with vigorous stirring. The organic layer was dried over anhydrous MgS0 4 • Concentration in vacuo gave the product in almost 100% yield. If desired, the product can be distilled at a low pressure through a very short column.
10 molar (n-BuLi). Apparatus: 1-1 round-bottomed, three-necked flask, equipped with a nitrogen inletthermometer combination, an efficient mechanical stirrer and an outlet; during the addition of iodine the outlet was replaced with a powder funnel. 10 mol of n-butyllithiurn in 64 ml of hexane was added over a few min by syringe, while keeping the temperature of the solution at --70 DC by occasional cooling in a bath with liquid nitrogen. The temperature was allowed to rise to -40 DC, after which 200 ml of diethyl ether was added.
Equipped with a nitrogen inletthermometer combination, an efficient, gas-tight mechanical stirrer and a cold finger filled with dry ice and acetone (for the preparation of the hypobromite solution the flask was equipped with a dropping funnel, a mechanical stirrer and a thermometeroutlet combination). Procedure: (Cf. L. D. 60 mol, 96 g) was added over -15 min to a vigorously stirred solution of 90 g of potassium hydroxide (technical quality, -15% H 20) in 200 ml of water, while keeping the temperature between -5 and 0 DC (bath with dry ice and acetone).
Application of Transition Metal Catalysts in Organic Synthesis by Prof. L. Brandsma, Prof. H. D. Verkruijsse, Prof. S. F. Vasilevsky (auth.)