Transition Metal Organometallics in Organic Synthesis by Howard Alper (Eds.)

By Howard Alper (Eds.)

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OLEFINIC 35 COMPOUNDS Ni/maleic anhydride catalyst A C 6 H 6 , 23°, 5 hr (90) ' (68%) Ni(cop) 2, P h 3p JC^y-y t C 6 H 6 , 2 5 ° , 24 hr ' / (91) (86%) /7— CN ff jy^// +4 . J\~7? CN (94) (95%) (1) R h C I 3, M e O C H 2C H 2O H , (2) N a C N Δ ' (95) PPh2 Mechanisms illustrating the possible types of processes involved in these reactions are suggested for the codimerization reaction [Eq. (87)] and the dimerization reaction [Eq. (90)] (Schemes 6 and 7). 36 ARTHUR J. BIRCH a n d IAN D. JENKINS Scheme 7 IV.

CN (94) (95%) (1) R h C I 3, M e O C H 2C H 2O H , (2) N a C N Δ ' (95) PPh2 Mechanisms illustrating the possible types of processes involved in these reactions are suggested for the codimerization reaction [Eq. (87)] and the dimerization reaction [Eq. (90)] (Schemes 6 and 7). 36 ARTHUR J. BIRCH a n d IAN D. JENKINS Scheme 7 IV. C - X B O N D F O R M A T I O N ( X = E L E M E N T O T H E R THAN CARBON) A . Nucleophilic Attack on Coordinated Double Bonds 1. Monoolefins. Wacker Process C - X bond formation by nucleophilic attack on coordinated olefins is in most respects analogous to C - C bond formation (Section IIIA).

R etc. Scheme 5 2. Oligomerization and Cyclooligomerization* In the reactions of olefins with olefins, different transition metal catalysts can give rise to markedly different products (Heimbach, 1973; Buchholz et ai, 1972; Kricka and Ledwith, 1974). Certain nickel catalysts, for example, normally trimerize butadiene as shown in Eq. (83) (Bogdanovic et ai, 1969). These same catalysts, however, in the presence of suitable ligands, will cyclodimerize butadiene to give initially divinylcyclobutane (which can be isolated in 4 0 % yield) and finally 1,5-cyclooctadiene in high yield [Eq.

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