By Prof. L. Brandsma, Prof. H. D. Verkruijsse, Prof. S. F. Vasilevsky (auth.)
Homogeneous catalysis is a vital approach for the synthesis of high-valued chemical substances. L. Brandsma has rigorously chosen and checked the experimental techniques illustrating the catalytic use of copper, nickel, and palladium compounds in natural synthesis. All systems are on a preparative scale, make monetary use of solvents and catalysts, steer clear of poisonous components and feature excessive yields.
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0 molar. Apparatus: 1-1 round-bottomed, three-necked flask, equipped with a dropping funnel, a mechanical stirrer and a combination of thermometer and outlet for the addition of bromine and the dehydrobromination; for the preparation of NaOCH 3 the same apparatus with a reflux condenser instead of the outlet-thermometer combination was used. 3 Olefinic, Cycloolefinic and Allenic Halides 37 densed. 0 mol, 160 g) was added dropwise over 45 min with cooling between -30 and -50 DC. After the addition, the diethyl ether was thoroughly removed at water-aspirator pressure.
A. A. Evans, J. Chern. Soc. (1950) 2014 and (1953) 2202. 7 (1H) ppm. l-Chlorocycloheptene was prepared in a similar way. 30 molar. 20 molar. ~ Br-CH 2-CH=CH-CH z-Br 0 ---7 20°C KOH Br-CH 2-CH=CH-CH z-Br Z petroleum ether + 2/3 H 3 P0 3 Z Br-CH=CH-CH=CH 2 ZIE - 10:90 (+ toJ ) Apparatus: I-I round-bottomed, three-necked flask, equipped with a dropping funnel, a mechanical stirrer and a thermometer-outlet combination for the preparation of 1,4-dibromo-2-butene; for the dehydrobromination a 2-1 round-bottomed, threenecked flask, equipped with an efficient, gas-tight mechanical stirrer was connected to a distillation apparatus consisting of a 30-cm Vigreux column, condenser and a 100-ml receiver cooled in a bath at -75°C.
0 mol, was added in portions of 25-30 ml from the dropping funnel, while cooling the flask in a bath with dry ice and acetone. After addition of each portion the solution became temporarily light -brown. Initially, the temperature of the efficiently stirred mixture was kept between ~10 and ~20 DC, but as the heating effect caused by further additions became less strong, the temperature of the mixture was gradually raised to between +10 and 20 DC (see Note 2). After completion of the addition stirring was continued for an additional period of ~3 h, during which the temperature was allowed to rise above 30 DC.
Application of Transition Metal Catalysts in Organic Synthesis by Prof. L. Brandsma, Prof. H. D. Verkruijsse, Prof. S. F. Vasilevsky (auth.)