Synthesis of octamethylferrocene derivatives via reaction of (octamethylferrocenyl)methyl carbocation with nucleophiles and application to functionalization of surfaces
- Massachusetts Institute of Technology, Cambridge (USA)
Formylation of octamethylferrocene, Fe(C{sub 5}Me{sub 4}H){sub 2}, using N,N{prime}-dimethylformamide/OPCl{sub 3} in CHCl{sub 3} solvent at 60-70{degree}C gives octamethylformylferrocene in high yield ({approximately} 95%). The aldehyde can be converted to a CN group to give octamethylcyanoferrocene or can be used to prepare ethyl {beta}-(octamethylferrocenyl)acrylate. Most important, reduction of octamethylformylferrocene using LiAlH{sub 4} in Et{sub 2}O yields the alcohol in {approximately} 95% yield. Acid-catalyzed (HBF{sub 4}) dehydration of the alcohol, leads for formation of (octamethylferrocenyl)methyl carbocation in almost quantitative yield. The carbocation can be isolated as an orange-red BF{sub 4}{sup {minus}} salt in {approximately} 90% yield from octamethylferrocene.
- OSTI ID:
- 6334183
- Journal Information:
- Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 112:21; ISSN 0002-7863; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
360601* -- Other Materials-- Preparation & Manufacture
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201 -- Chemical & Physicochemical Properties
CHEMICAL PREPARATION
COMPLEXES
DATA
DIENES
ELECTRODES
EXPERIMENTAL DATA
FERROCENE
HYDROCARBONS
INFORMATION
IRON COMPLEXES
MEASURING METHODS
MEDIUM TEMPERATURE
NUMERICAL DATA
ORGANIC COMPOUNDS
POLYENES
SURFACE TREATMENTS
SYNTHESIS
TRANSITION ELEMENT COMPLEXES