1993
DOI: 10.1016/0022-328x(93)83414-q
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A simple synthesis of metallocene aldehydes from lithiometallocenes and N,N-dimethylformamide: Ferrocene and ruthenocene aldehydes and 1,1′-dialdehydes

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Cited by 82 publications
(38 citation statements)
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“…To synthesize new metallocenic heterocyclic compounds, we have chosen in first to exploit the reactivity in basic medium of the easy accessible 2,6-diphenyl-4H-pyran-4-yl triphenylphosphonium tetrafluoroborate salt [14] with ferrocenecarboxaldehyde and ferrocene-1,1 0 -dicarboxaldehyde [15]. At À78°C, addition of formylferrocene to a THF solution of the heterocyclic phosphorane, generated in situ by reaction of the phosphonium salt with n-BuLi (2.5 M solution in hexane), afforded the ferrocenyl methylenepyran 1 in good yield.…”
Section: Results and Discussion: Synthesis Of The Pyran Compoundsmentioning
confidence: 99%
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“…To synthesize new metallocenic heterocyclic compounds, we have chosen in first to exploit the reactivity in basic medium of the easy accessible 2,6-diphenyl-4H-pyran-4-yl triphenylphosphonium tetrafluoroborate salt [14] with ferrocenecarboxaldehyde and ferrocene-1,1 0 -dicarboxaldehyde [15]. At À78°C, addition of formylferrocene to a THF solution of the heterocyclic phosphorane, generated in situ by reaction of the phosphonium salt with n-BuLi (2.5 M solution in hexane), afforded the ferrocenyl methylenepyran 1 in good yield.…”
Section: Results and Discussion: Synthesis Of The Pyran Compoundsmentioning
confidence: 99%
“…Ferrocene-1,1 0 -dicarboxaldehyde was obtained from Ref. [15] and mono-protected ferrocene-1,1 0 -dicarboxaldehyde was synthesized as described previously by Balavoine and coll. [16].…”
Section: Methodsmentioning
confidence: 99%
“…DMF purchased from Aldrich and freshly distilled prior to use. Mono and 1, 1 0 -dihydroxymethyl ferrocene complexes, 1a-b were prepared according to the literature [35,36]. Chromatography was carried out on 3 cm of silica gel in a 2.5 cm diameter column.…”
Section: General Procedures and Instrumentationmentioning
confidence: 99%
“…[67,68] Ruthenocene (2.0 mmol, 0.46 g) was dissolved in hexane (40 ml) and treated with a 2.2 fold excess of 77-butyl-lithium (2.75 ml of the 1.6 M commercial hexane solution) in the presence of tmeda (4.4 mmol, 0.66 ml). The slightly green-yellow solution was stirred overnight (16 h) to give a white suspension.…”
Section: Synthesesmentioning
confidence: 99%