1992
DOI: 10.1080/02678299208030396
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Synthesis and thermal properties of mesomorphic 1,1′-bis[ω-(4′-cyano-4-biphenyloxy)alkyl] ferrocenes

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Cited by 32 publications
(8 citation statements)
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“…Although AlCl 3 is the most commonly used Lewis acid for this reaction, we chose to use BF 3 · OEt 2 23b because, whereas AlCl 3 often gives a mixture of the mono‐ and diacylated product, it is known that only monoacylation occurs with this Lewis acid 23b. It must be mentioned that irrespective of the Lewis acid used, Zn‐powder was required for the acylation process with ω‐bromoacid chlorides, because, as Bhatt et al23a reported in 1992, either decomposition (black‐coloring of solution) or oxidation of the ferrocene unit was observed in the absence of elemental Zn.…”
Section: Resultsmentioning
confidence: 99%
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“…Although AlCl 3 is the most commonly used Lewis acid for this reaction, we chose to use BF 3 · OEt 2 23b because, whereas AlCl 3 often gives a mixture of the mono‐ and diacylated product, it is known that only monoacylation occurs with this Lewis acid 23b. It must be mentioned that irrespective of the Lewis acid used, Zn‐powder was required for the acylation process with ω‐bromoacid chlorides, because, as Bhatt et al23a reported in 1992, either decomposition (black‐coloring of solution) or oxidation of the ferrocene unit was observed in the absence of elemental Zn.…”
Section: Resultsmentioning
confidence: 99%
“…Moreover, the reversibility of the ferrocene/ferrocenium redox couple21 and electronic stabilization of adjacent electron‐deficient centers due to participation of the iron atom in the stabilization of the positive charge21,22 seemed to be attractive. The air‐stability of many ferrocene derivatives, as well as a huge number of applicable organic reactions, such as acylation,23 coupling chemistry24 or reduction,23a,25 were also considered to be beneficial in this context.…”
Section: Introductionmentioning
confidence: 99%
“…We anticipated that base‐promoted elimination of HBr from (bromopropionyl)ferrocene 2 and 1,1′‐bis(bromopropionyl)ferrocene would furnish acryloylferrocene and diacryloylferrocene, respectively. For this purpose, we easily accessed 2 and 3 from ferrocene via Friedel–Crafts acylation of ferrocene with bromopropionyl chloride 13. Reaction of (bromopropionyl)ferrocene ( 2 ) with Et 3 N (1.5 equiv., CH 3 CN, 28 °C, 10 min) led to the formation of 4 in 96 % yield.…”
Section: Resultsmentioning
confidence: 99%
“…12 The starting materials, 1,1'-bis(ω-bromoalkyl)ferrocenes, were prepared by Friedel-Crafts acylation of ferrocene with ωbromoacyl chlorides and subsequent reduction of the obtained 1,1'-acylferrocenes 1a,b. 13 The crystal structure of 1,1'-bis(5bromopentanoyl)ferrocene (1b) shows no unusual features and can be found in the Electronic Supplementary Information (ESI). Treatment of two equivalents of 1-phenylphospholane with 1,1'-bis(ω-bromoalkyl)ferrocenes 2a,b gave the corresponding phosphonium salts 3a and 3b in quantitative yield as orange solids.…”
Section: Resultsmentioning
confidence: 99%