By Christian Bruneau, Pierre Dixneuf
With specialize in the purposes in synthesis and catalysis, this booklet comprehensively discusses themes starting from polymerization to metathesis, from molecular fabrics to carbon wealthy compounds together with how those compounds play the most function within the metathesis response, the 2005 Nobel Prize subject.
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Additional info for Metal Vinylidenes and Allenylidenes in Catalysis: From Reactivity to Applications in Synthesis
Sample text
Addition of SPhÀ to [Fe(¼C¼CMe2)(CO)(PPh3)Cp]þ gives Fe{C(SPh)¼CMe2} (CO)(PPh3)Cp; a 93/7 Z/E mixture is formed with the ¼C¼CMePh complex [287]. The reaction of [S2CNEt2]À with RuCl{¼C¼CH(tol)}(PPh3)Tp gives Ru{C[¼CH(tol) SC(NEt2)S]}(PPh3)Tp [128, 287]. Treatment of TaH(¼C¼CH2)CpÃ2 with Group 16 nucleophiles (H2O, MeOH, RCH2SH) results in elimination of C2H4 and formation of CpÃ2TaH(X) (X ¼ O, Z2-CH2O, Z2-CHRS, respectively) [280, 288]. 5 Group 15 Nucleophiles. 17): Ln M¼C¼CR1 R2 þ NHR3 R4 ! Ln M¼CðNR3 R4 ÞCHR1 R2 ð1:17Þ for example, MLn ¼ Fe(CO)(PPh3)Cp [9b], RuCl2(pnp) [289], RuCl{PPh2(o-tol)} Cp [116], W(CO)(NO)Cp [290, 291].
Me2Si Me2 Si C (Me2Si)n O C {Mn(CO)2Cp} Si Me2 3 Me2 Si Me2 Si O SiMe 2 Me2Si Fe(CO)3 O O Si Me2 Si Me2 4 Unusual iron-porphyrin vinylidene complexes were obtained from DDT [1,1-bis(4chlorophenyl)-2,2,2-trichloroethane] and Fe(tpp) [tpp ¼ meso-tetraphenylporphinato (2-)] in the presence of a reducing agent [10a, 264]. The derived N,N0 -vinylene-bridged porphyrin reacts with metal carbonyls [Fe3(CO)12, Ru3(CO)12] to break one or both NÀC bonds with insertion of the vinylidene into an MÀN bond. While the iron complex was formed in 90% yield, the reaction with Ru3(CO)12 afforded three products, the vinylidene being formed in only 40% yield [265].
Reductive uncoupling also occurs, making these systems of interest as potential energy sinks [142]. Oxidation [PhIO or Cu(OAc)2] of [Fe(¼C¼CHMe)(dppe)Cp]þ affords bis(vinylidene) [{Fe(dppe)Cp}2(m-C4Me2)]2þ, possibly via an intermediate radical cation [222]. Similar oxidative coupling of cyclopropenyl Ru{C¼CPhCH(CN)}(PPh3)2Cp affords bis(vinylidene) [{Cp(Ph3P)2Ru}¼C¼CPhCH(CN)2}2]2þ which, in turn, can be deprotonated to the bis(cyclopropenyl) [223]. Oxidation of [Ru(N4Me8)(¼C¼CH2)]2À with PhN3 or [FeCp2]þ affords [{Ru(N4Me8)}2(m-C¼CHCH¼C)]4À [51].