1,3-Dipolar cycloaddition to the iron-imine (Fe-N:C) fragment. 8. Formation of 1,4,3a,6a-tetrahydropyrrolo[3,2-b]pyrroles via double 1,3-dipolar cycloaddition of alkynes to Fe(CO)2(CNR)(.alpha.-diimine). Competition between isocyanide and CO insertion. Determination of cone angles of isocyanides

Lange, Paul P.; Fruhauf, Hans Werner; Kraakman, M. J. A.; Wijnkoop, Maarten van; Kranenburg, Mirko; Groot, A. H. J. P.; Vrieze, K.; Fraanje, Jan; Wang, Yuan-Fang; Numan, Milco

doi:10.1021/om00026a029

Cited by 30 publications

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“…Cooling the pentane solution to − 30°C resulted in a voluminous precipitate of the excess free Et 4 -DTO ligand. Filtration gave a deep green-blue solution containing a mixture of the mononuclear complex Fe(CO) 3 (Et 4 -DTO) (7d) and the The co-ordination behaviour of several R 2 -and R 4 -DTO ligands to Mo(CO) 4 − n (PR 3 ) n has been studied by tom Dieck et al [18,19]. For n = 0, 1, they found that the DTO ligand acts as a relatively strong donor and for n=2, the R 2 -and R 4 -DTO ligand acts as good p-acceptor ligand.…”

Section: Synthesis Of Fe(co) 3 (Et 4 -Dto) (7d)mentioning

confidence: 99%

“…In the case of ligands a -d, initially, the deep green or blue Fe(CO) 3 (DTO) complexes (7) are observed before they react further with [FeCO) 4 ] to three different types of Fe 2 (CO) 6 (DTO) complexes 8. The reactions of 7a and 7d with DMAD have been studied.…”

Section: Synthesis Of Fe(co) 3 (Et 4 -Dto) (7d)mentioning

confidence: 99%

“…In the case of the reaction with ligands b and c, the initial deep green-blue Fe(CO) 3 (DTO) complexes 7b,c are formed in low stationary concentrations because they directly react further with [Fe(CO) 4 ] to form the dimeric Fe 2 (CO) 6 [R%N C(S) (S)C(H)N(H)R%] complexes 8b,c in high yield. The two sulfur atoms of the modified DTO ligand in complexes 8b,c are reduced to sulfido groups which are bridging between the two Fe(CO) 3 fragments (m 2 -S co-ordination), thus acting as a six-electron donor.…”

Section: Synthesis Of Mononuclear |-S |-S% Chelate Complexes Fe(co)mentioning

confidence: 99%

“…In the last decade, the reactions of the mononuclear M(CO) n (CNR) 3 − n (R-DAB) complexes (M= Fe, Ru; n= 0, 1, 3) [1][2][3][4][5][6][7][8] with the alkynes DMAD and MP have been studied extensively in our laboratory. These reactions have been shown to give some interesting highly functionalised coordinated heterocyclic ligands such as in complexes 4 and 5 (cf.…”

Section: Introductionmentioning

confidence: 99%

“…Fe 2 (CO) 9 [34] 1 has been prepared according to the published procedure. The ligands cyclo-DTO [35] (a), R 2 -DTO (b, c) [36] and Et 4 -DTO (d) [36] were prepared according to published procedures.…”

Section: Introductionmentioning

confidence: 99%

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1,3-Dipolar cycloaddition to the FeSC fragment 20. Preparation and properties of carbonyliron complexes of di-thiooxamide. Reactivity of the mononuclear (di-thiooxamide)Fe(CO)3 towards dimethyl acetylenedicarboxylate

Siebenlist

Frühauf

Kooijman

et al. 2002

Inorganica Chimica Acta

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Section: Synthesis Of Fe(co) 3 (Et 4 -Dto) (7d)mentioning

confidence: 99%

Section: Synthesis Of Fe(co) 3 (Et 4 -Dto) (7d)mentioning

confidence: 99%

Section: Synthesis Of Mononuclear |-S |-S% Chelate Complexes Fe(co)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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1,3-Dipolar cycloaddition to the FeSC fragment 20. Preparation and properties of carbonyliron complexes of di-thiooxamide. Reactivity of the mononuclear (di-thiooxamide)Fe(CO)3 towards dimethyl acetylenedicarboxylate

Siebenlist

Frühauf

Kooijman

et al. 2002

Inorganica Chimica Acta

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Preparation and Properties of Carbonyliron Complexes of 1-Aza-4-oxa-1,3-butadiene (α-Imino Ketone) – X-ray Crystal Structures of Fe(CO)3[MeNC(Ph)C(Ph)=O] and Fe2(CO)4[tBuNC(H)(Me)C(O)(O)C(Me)C(H)=NtBu]

Siebenlist¹,

Frühauf²,

Vrieze³

et al. 2000

Eur. J. Inorg. Chem.

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The reaction of Fe2(CO)9 at room temperature in THF or toluene with the α‐imino ketones R1N=C(R2)–C(R3)=O (L) (R1 = alkyl, R2 = H, Me, Ph, R3 = Me, Ph) (a–k), initially results in the formation of the mononuclear chelate Fe(CO)3(α‐imino ketone) complexes 6 which can be isolated in moderate (6h) to high (6e–g) yield. Under these reaction conditions, complexes 6 subsequently react with [Fe(CO)4] fragments or dimerise, to form the dinuclear complexes Fe2(CO)6(α‐imino ketone) (7a–j) or Fe2(CO)4(L–L) (8a,b,k), respectively. The complexes 8 contain two α‐imino ketone ligands C–C coupled at the ketone carbon atoms. Complexes 8a,b react with CO at elevated temperatures to quantitatively yield Fe(CO)3(α‐imino ketone) (6a,b). This reaction can be reversed photochemically. Irradiation of a solution of 6a,b in the low‐energy band results in the reformation of 8a,b in almost quantitative yield. The extremely air‐sensitive complexes 6 and the dinuclear complexes 7 and 8 have been characterised spectroscopically (IR, UV/Vis, 1H and 13C NMR) and by elemental analysis. The solid state structures of complexes 6g and 8a have been determined by single‐crystal X‐ray diffraction. The molecular structure of 6g confirms the flat σ‐O,σ‐N chelate coordination of the α‐imino ketone. The structure of 8a consists of two metal–metal‐bonded Fe(CO)2 units, bridged by a formally 10e‐donating dianionic C–C coupled (tBu‐ADO) ligand. A mechanism for the formation of complexes 8 is discussed.

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Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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1,3-Dipolar cycloaddition to the iron-imine (Fe-N:C) fragment. 8. Formation of 1,4,3a,6a-tetrahydropyrrolo[3,2-b]pyrroles via double 1,3-dipolar cycloaddition of alkynes to Fe(CO)2(CNR)(.alpha.-diimine). Competition between isocyanide and CO insertion. Determination of cone angles of isocyanides

Cited by 30 publications

References 0 publications

1,3-Dipolar cycloaddition to the FeSC fragment 20. Preparation and properties of carbonyliron complexes of di-thiooxamide. Reactivity of the mononuclear (di-thiooxamide)Fe(CO)3 towards dimethyl acetylenedicarboxylate

1,3-Dipolar cycloaddition to the FeSC fragment 20. Preparation and properties of carbonyliron complexes of di-thiooxamide. Reactivity of the mononuclear (di-thiooxamide)Fe(CO)3 towards dimethyl acetylenedicarboxylate

Preparation and Properties of Carbonyliron Complexes of 1-Aza-4-oxa-1,3-butadiene (α-Imino Ketone) – X-ray Crystal Structures of Fe(CO)3[MeNC(Ph)C(Ph)=O] and Fe2(CO)4[tBuNC(H)(Me)C(O)(O)C(Me)C(H)=NtBu]

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

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