1,1′‐Diaminoferrocene

Shafir, Alexandr; Power, Maurice P.; Whitener, Glenn D.; Arnold, John; Miller, Philip W.; Long, Nicholas J.

doi:10.1002/9781118744994.ch14

Cited by 8 publications

(5 citation statements)

References 36 publications

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“…All other commercially available compounds were purchased from Sigma-Aldrich and used as received. N , N -Dimethyl- p -xylylenediamine, [Ae(N(SiMe 3 ) 2 ) 2 ·(THF) 2 ] (Ae = Ca, Sr, Ba), − [Ba(CH(SiMe 3 ) 2 ) 2 ·(THF) 2 ], 1,1′-bis(amino)ferrocene, − and ruthenocene were synthesized according to published procedures.…”

Section: Methodsmentioning

confidence: 99%

Ferrocene-Containing Polycarbosilazanes via the Alkaline-Earth-Catalyzed Dehydrocoupling of Silanes and Amines

et al. 2019

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We report the use of the alkaline-earth (Ae) metalcatalyzed dehydrocoupling of silanes and amines for the synthesis of ferrocene-containing polycarbosilazanes. The barium complex [Ba(N(SiMe 3 ) 2 ) 2 •(THF) 2 ] catalyzed the dehydrocoupling of the hydrosilane FeCp(CpSiPhH 2 ) (1) with 1,4-(H 2 NCH 2 ) 2 C 6 H 4 under mild conditions to give a polycarbosilazane with pendant ferrocene groups. The polymer could be readily cross-linked by the addition of phenylsilane to the unquenched reaction mixture. Welldefined polycarbosilazanes with ferrocene in the main chain were also obtained from the dehydrocoupling of hydrosilanes Fe(Cp-(SiPhH 2 )) 2 (3) and Fe(Cp(SiMe 2 H)) 2 (IX) with 1,4-(H(Me)-NCH 2 ) 2 C 6 H 4 and 1,4-(H 2 NCH 2 ) 2 C 6 H 4 , respectively. Crystalline monomeric analogues, FeCp(Cp(SiPh(NHBn) 2 )) (2, Bn = CH 2 (C 6 H 5 )), and Fe(Cp(SiPh(NHBn) 2 )) 2 (4), were also obtained via the dehydrocoupling benzylamine with 1 and 3, respectively. The barium-catalyzed dehydrocoupling of diaminoferrocene with Ph 2 SiH 2 or Ph(Rc)SiH 2 (6, Rc = (C 5 H 4 )Ru(C 5 H 5 )) did not result in polymer, but instead in the formation of the silazanebridged ansa-[3]ferrocenophanes (Fe(η-C 5 H 4 NH) 2 SiPh 2 ) (5) and (Fe(η-C 5 H 4 NH) 2 SiPh(Rc)) (7), respectively. Both polymeric and molecular products were electrochemically investigated, and the polymers proved to be promising precursors to magnetic iron-containing ceramics in yields of up to 64%.

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Section: Methodsmentioning

confidence: 99%

Ferrocene-Containing Polycarbosilazanes via the Alkaline-Earth-Catalyzed Dehydrocoupling of Silanes and Amines

et al. 2019

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“…The synthesis and chemistry of 1,1'-and 1,2-disubstituted ferrocene compounds remains an important area of study because of the numerous applications of these compounds in organic synthesis, materials science and medicine. [1][2][3][4][5][6][7][8][9][10] Key to the synthesis of such compounds has been the preparation of suitable versatile precursors such as bromoferrocenes. In the case of 1,1'-dibromoferrocene, which is a key precursor, there are now many suitable reaction protocols allowing its practical synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structures of 1,1′,2-Tribromoferrocene, 1,1′,2,2′-Tetrabromoferrocene, 1,1′,2,2′-Tetrabromoruthenocene: Expanding the Range of Precursors for the Metallocene Chemist’s Toolkit

et al. 2021

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The synthesis, characterisation, and isolation of 1,1′,2-tribromoferrocene and 1,1′,2,2′-tetrabromoferrocene, which are key synthons in ferrocene chemistry, are described. These compounds are prepared using α-halide assisted lithiation. The crystal structures of 1,1′,2-tribromoferrocene, 1,1′,2,2′-tetrabromoferrocene, 1,1′-dibromoruthenocene, and 1,1′,2,2′-tetrabromoruthenocene have been determined and are reported together with a brief discussion of the intramolecular forces involved in the crystal structures.

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“…3 Arguably the most synthetically useful compound has been the 1,1´dilithioferrocene.TMEDA complex, 4 which is used in the preparation of a wide range of disubstituted ferrocenes, prominent among these being the well-used ligand dppf, 5 1,1´-ferrocenedicarboxylic acid, 6 ferrocene-1,1´-dicarbaldehyde, 7 and 1,1´-dibromoferrocene. 8 The latter compound, in turn, serves as a precursor to pure 1,1´-dilithioferrocene. 9 We have developed the synthesis of ortho-lithiated derivatives 10 of the bromoferrocene and 1,1´-dibromoferrocene and this work has been augmented in several recent papers from other research groups, and this has turned into an active area of ferrocene synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…The mechanism of lithiation has been examined . Arguably the most synthetically useful compound has been the 1,1′-dilithioferrocene·TMEDA complex, which is used in the preparation of a wide range of disubstituted ferrocenes, prominent among these being the well-used ligand dppf, 1,1′-ferrocenedicarboxylic acid, ferrocene-1,1′-dicarbaldehyde, and 1,1′-dibromoferrocene . The last compound, in turn, serves as a precursor to pure 1,1′-dilithioferrocene .…”

Section: Introductionmentioning

confidence: 99%

1,1′,2,2′-Tetralithioferrocene and 1,1′,2,2′,3,3′-Hexalithioferrocene: Useful Additions to Ferrocene Precursor Compounds

et al. 2021

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The direct synthesis of 1,1´,2,2´-tetralithioferrocene from 1,1´,2,2´-tetrabromoferrocene is reported. In addition, the related 1,1´,2,2´,3,3´-hexalithioferrocene is also described, prepared directly from 1,1´,2,2´,3,3´-hexabromoferrocene. These lithioferrocenes may be isolated as orange red (tetralithio-) and red (hexalithio-) powders, respectively. When these are prepared in situ and reacted with chlorotrimethylsilane, the corresponding tetrakis-1,1´,2,2´-tetrakis(trimethylsilyl)ferrocene and 1,1´,2,2´,3,3´-hexakis(trimethylsilyl)ferrocene are obtained as red and crimson crystalline solids respectively. The single crystal structures of 1,1´,2,2´-tetrakis(trimethylsilyl)ferrocene, 11, and 1,1´,2,2´,3,3´-hexakis(trimethylsilyl)ferrocene, 12, have been determined and are described.

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1,1′‐Diaminoferrocene

Cited by 8 publications

References 36 publications

Ferrocene-Containing Polycarbosilazanes via the Alkaline-Earth-Catalyzed Dehydrocoupling of Silanes and Amines

Ferrocene-Containing Polycarbosilazanes via the Alkaline-Earth-Catalyzed Dehydrocoupling of Silanes and Amines

Synthesis and Structures of 1,1′,2-Tribromoferrocene, 1,1′,2,2′-Tetrabromoferrocene, 1,1′,2,2′-Tetrabromoruthenocene: Expanding the Range of Precursors for the Metallocene Chemist’s Toolkit

1,1′,2,2′-Tetralithioferrocene and 1,1′,2,2′,3,3′-Hexalithioferrocene: Useful Additions to Ferrocene Precursor Compounds

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