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Extra so than any of the opposite significant teams of parts within the periodic desk, the transition metals have formed human historical past and feature been the workhorses of undefined. the invention of steel copper ended the Stone Age and ushered within the Bronze Age. Alloys of iron (especially metal) later took over, and the Iron Age changed the Bronze Age.
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2-alkylcyclohexadiene complexes are more stable than the 1-alkyl ones (A. J. Birch, B. J. Chauncy, and D . J. Thompson, unpublished results; A. J. Birch, C. S. Sell, and I. D . Jenkins, unpublished results). This equilibrium can lead to further synthetic possibilities, not possible with the uncomplexed dienes. B. Olefin Disproportionation (Exchange of Alkylidene Groups) Transition metal-catalyzed olefin disproportionation [Eq. (149) (R = alkyl, aryl ; R = heteroatom such as CI deactivates the double bond toward the metathesis reaction)] has been used very little in organic synthesis, but the reaction has considerable potential and has been the subject of several reviews (Banks, 1972; Calderon, 1972; Hughes, 1972; Cardin et ai, 1973; Haines and Leigh, 1975).
Rigorous exclusion of air and moisture, and pure olefins and solvents are necessary. The olefin disproportionation reaction attains a thermodynamic equilibrium with respect to both the exchange of alkylidene groups and the cis/trans isomer distribution of the component olefins. The reversible nature of the reaction limits its use in organic synthesis except in those cases where one of the component olefins (for example, ethylene) is readily removed from the reaction mixture. Some examples of alkylidene exchange reactions are shown in Eqs.
More recently, a hydrogénation procedure for ferrocenes employing Pd/C as catalyst under mild conditions (1 atm hydrogen, room temperature) but in acid solution (aqueous perchloric acid in acetic acid) has been reported as a synthetic route to substituted cyclopentanes. N o yields were given (Van Meurs et ai, 1975). Tricarbonyl(cyclobutadiene)iron is also readily acylated as shown in Eq. (68) (Fitzpatrick et ai, 1965), thus providing easy access to substituted cyclobutadienes by removal of the tricarbonyliron group with eerie ion (Section VI,A).
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