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Reactions of alkynes with [Fe-2(CO)(6)(mu-PPh2){mu-eta(1):eta(2)(alpha,beta)-(H)C-alpha = C-beta = C gamma H-2}]: Formation of diphenylvinylphosphine-functionalized vinyl carbenes via carbon-carbon and carbon-phosphorus bond formation and hydrogen migration

Doherty, S; Hogarth, G; Waugh, M; Clegg, W; Elsegood, MRJ; (2000) Reactions of alkynes with [Fe-2(CO)(6)(mu-PPh2){mu-eta(1):eta(2)(alpha,beta)-(H)C-alpha = C-beta = C gamma H-2}]: Formation of diphenylvinylphosphine-functionalized vinyl carbenes via carbon-carbon and carbon-phosphorus bond formation and hydrogen migration. ORGANOMETALLICS , 19 (22) 4557 - 4562. 10.1021/om0005147.

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Abstract

Reaction of [Fe-2(CO)(6)(mu-PPh2){mu-eta(1):eta(alpha,beta-)(2)(H)C-alpha=C-beta=CgammaH2}] (1) with PhC=CPh results in allenyl-alkyne-phosphido coupling to give [Fe-2(CO)(6)(mu-PPh2){mu-eta(1)(P):eta(3)(C):eta(1)(C)-C(Ph)C(Ph)C(H)C(=CH2)PPh2}] (2), bridged by a diphenylvinylphosphine-substituted vinyl carbene. Under similar conditions 1 reacts with PhC=CMe to give an equal mixture of the two possible regioisomers, [Fe-2(CO)(6)(mu-PPh2){mu-eta(1)(P):eta(3)(C):eta(1)(C)-C(Ph)C(Me)C(H)C(=CH2)PPH2}] (3a) and [Fe-2(CO)(6)(mu-PPh2){mu-eta(1)(P):eta(3)(C):eta(1)(C)-C(Me)C(Ph)C(H)C(=CH2)PPh2}] (3b). In contrast, 1 reacts with 2 equiv of PhC=CH to give the vinyl carbene bridged [Fe-2(CO)(6)(mu-PPh2){mu-eta(1)(P):eta(3)(C):eta(1)(C)-(Ph)CCC(H)MeCH=CPhC(PPh2)}] (4), which results from a complex sequence of carbon-carbon and carbon-phosphorus bond formation and hydrogen migration steps.

Type:Article
Title:Reactions of alkynes with [Fe-2(CO)(6)(mu-PPh2){mu-eta(1):eta(2)(alpha,beta)-(H)C-alpha = C-beta = C gamma H-2}]: Formation of diphenylvinylphosphine-functionalized vinyl carbenes via carbon-carbon and carbon-phosphorus bond formation and hydrogen migration
DOI:10.1021/om0005147
Keywords:RAY CRYSTAL-STRUCTURES, ALLENYL COMPLEXES, REGIOSELECTIVE ADDITION, NUCLEOPHILIC-ADDITION, PHOSPHIDO BRIDGE, C-ALPHA, REACTIVITY, INSERTION, CHEMISTRY, LIGANDS
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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