Synthesis, structure and characterization of some Schiff bases bearing phenylferrocene

Shah, Faiz Ullah; Akhter, Zareen; Siddiqi, Humaira M.; Parvez, Masood

doi:10.1002/aoc.1255

Cited by 5 publications

(2 citation statements)

References 15 publications

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“…The W1−C14, W1−C5, and W1−N2 bond lengths in 4a are indicative of single σ-bonds . The C5−N2 interatomic distance of 1.257(10) Å indicates a carbon−nitrogen bond order similar to that extant in free imines . Consequently, the bonding of the iminoacyl ligand to the tungsten center in 4a is best described as consisting of a W−C σ-bond and a W←N dative interaction that provides a total of three electrons necessary for the Cp*W(NO)(alkyl) fragment to achieve an 18e configuration while leaving the C−N multiple bond unperturbed.…”

Section: Resultsmentioning

confidence: 99%

Toward Alkane Functionalization Effected with Cp*W(NO)(alkyl)(η³-allyl) Complexes

et al. 2009

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Cp*W(NO)(n-alkyl)(η3-allyl) complexes result from the selective activations of the terminal C−H bonds of alkanes. Consequently, the reactions of prototypical members of this family of complexes with a range of electrophiles and nucleophiles have been explored with a view to developing methods for functionalizing the newly formed alkyl ligands. The two principal complexes investigated in this regard have been Cp*W(NO)(CH2SiMe3)(η3-CH2CHCHMe) (1) and Cp*W(NO)(CH2C6H5)(η3-CH2CHCHMe) (2). It has been found that treatment of 1 and 2 with the oxidant I2 at −60 °C produces Cp*W(NO)I2 and terminally functionalized ICH2SiMe3 and ICH2C6H5, respectively. Oxidation of 1 by H2O2 also results in the loss of the allyl ligand and production of the known oxo peroxo complex Cp*W(O)(η2-O2)(CH2SiMe3). Treatment of 1 and 2 with electrophiles affords the products resulting from addition of the electrophile to the electron-rich terminus of the σ−π distorted allyl ligands in the reactants. Thus, reagents of the type E-X (E = triphenylcarbenium, H, catecholborane; X = Cl, BF4) liberate CH3CHCHCH2E and form the organometallic products Cp*W(NO)(X)(CH2SiMe3) and Cp*W(NO)(X)(CH2C6H5), respectively. Exposure of the tungsten alkyl allyl complexes to isocyanide reagents leads to the formation of complexes bearing β,γ-unsaturated η2-iminoacyl ligands that apparently arise from the migratory insertion of isocyanide into the tungsten−allyl linkages. For instance, reaction of 1 with 2,6-xylylisocyanide produces Cp*W(NO)(CH2SiMe3)(η2-CH3CHCHCH2CNC6H3Me2) (4a). Interestingly, gentle heating or chromatography of 4a causes isomerization of the olefin and conversion to the conjugated product Cp*W(NO)(CH2SiMe3)(η2-CH3CH2CHCHCNC6H3Me2) (4b). A similar reaction of 2 with 2,6-xylylisocyanide affords both unconjugated and conjugated isocyanide insertion products, while treatment of 2 with n-butylisocyanide produces primarily the conjugated product. Finally, exposure of these tungsten alkyl allyl complexes to 1000 psi of CO gas generally results in the desired migratory insertion of the CO into the metal−alkyl linkages to form acyl compounds. Hence, 1 is first converted into Cp*W(NO)(C(O)CH2SiMe3)(η3-CH2CHCHMe), which then subsequently transforms into isolable Cp*W(NO)(C(O)CH3)(η3-CH2CHCHMe) (7). Interestingly, 2 does not react with CO under these experimental conditions. Nevertheless, the generality of this mode of reactivity is established by the fact that similar treatment of four other Cp*(W)(NO)(CH2CMe3)(η3-allyl) complexes with CO gas at elevated pressures does afford the corresponding acyl products (8−11). All new organometallic complexes have been characterized by conventional spectroscopic and analytical methods, and the solid-state molecular structures of several compounds have been established by X-ray crystallographic analyses.

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Section: Resultsmentioning

confidence: 99%

Toward Alkane Functionalization Effected with Cp*W(NO)(alkyl)(η³-allyl) Complexes

et al. 2009

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“…For similar structures, see: Fukuzumi et al (2002); Shah et al (2007). For graph-set notation, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

N-(4-Ferrocenylphenyl)benzamide

Altaf¹,

Badshah²,

Khan³

et al. 2010

Acta Cryst E

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In the title compound, [Fe(C5H5)(C18H14NO)], the unsubstituted cyclopentadienyl ring is disordered over two sets of sites with occupancy ratio of 0.55 (1):0.45 (1). One conformation has the rings eclipsed and the other staggered. An intramolecular C—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, intermolecular C—H⋯O and N—H⋯O hydrogen bonds lead to R 2 1(7) ring motifs. The molecules are linked into polymeric chains extending along the b axis.

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Pyrrole thioamide complexes of the d8 metals platinum(II), palladium(II) and gold(III)

Tang

Saunders

et al. 2020

Inorganica Chimica Acta

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Synthesis, structure and characterization of some Schiff bases bearing phenylferrocene

Cited by 5 publications

References 15 publications

Toward Alkane Functionalization Effected with Cp*W(NO)(alkyl)(η³-allyl) Complexes

Toward Alkane Functionalization Effected with Cp*W(NO)(alkyl)(η³-allyl) Complexes

N-(4-Ferrocenylphenyl)benzamide

Pyrrole thioamide complexes of the d8 metals platinum(II), palladium(II) and gold(III)

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Synthesis, structure and characterization of some Schiff bases bearing phenylferrocene

Cited by 5 publications

References 15 publications

Toward Alkane Functionalization Effected with Cp*W(NO)(alkyl)(η3-allyl) Complexes

Toward Alkane Functionalization Effected with Cp*W(NO)(alkyl)(η3-allyl) Complexes

N-(4-Ferrocenylphenyl)benzamide

Pyrrole thioamide complexes of the d8 metals platinum(II), palladium(II) and gold(III)

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Toward Alkane Functionalization Effected with Cp*W(NO)(alkyl)(η³-allyl) Complexes

Toward Alkane Functionalization Effected with Cp*W(NO)(alkyl)(η³-allyl) Complexes