Date of Award
Bachelor of Science
William B. Martin, Jr.
The discovery of ferrocene, bis-cyclopentadienyl iron, in 1951 stimulated further research into a relatively new field of Organic Chemistry, organometallies. Ferrocene is the first of a series of transition metal-organic ring compounds in which the metallic atom is bound covalently to two cyclopentadiene rings (Fig III). The rings are superimposed over one another with the single atom inbetween; thus, they are often referred to as “sandwich compounds.” The following procedure is that which Rinehart (11) used to prepare the acid derivative β-ferrocenoylpropionic acid (VII). The preparation consists of adding 7.4 g. of ferrocene and 2.0 g. of succinic anhydride in 150 ml. of methylene chloride to 5.8 g. of aluminum chloride in 150 ml. of methylene chloride. The reaction was stirred for two hours at room temperature, then decanted over ice. The crude acid was extracted from methylene chloride with sodium carbonate, filtered through Celite, and reprecipitated with dilute hydrochloric acid. The orange acid was recrystallized from methanol-bensene. Results of elemental analysis for carbon, hydrogen, and iron, and infra-red data supported the proposed structure (VIII).
Grand, Arthur F., "The preparation of 1, 1'tetramethylene ferrocene" (1963). Honors Theses. 1778.