Preparation of seven high-molecular-weight (C30-C40) hydrocarbons containing two and four gem-dimethyl units interspersed in the aliphatic chain are described. Addition of mono-and difunctional Grignard reagents to ethyl isopropylidenemalonate was employed to incorporate gem-dimethyl units into key intermediates. The use of difunctional Grignard reagents in this reaction has not been previously reported. The acid chlorideorganocadmium reaction was better for the preparation of diketone intermediates than the Grignard-nitrile reaction. A three-step procedure of reduction, dehydration, and hydrogenation to convert the diketone intermediates to the desired hydrocarbons was found to be superior to direct Wolff-Kishner reduction.
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