Synthesis of octamethylferrocene derivatives via reaction of (octamethylferrocenyl)methyl carbocation with nucleophiles and application to functionalization of surfaces

Journal Article · Wed Oct 10 00:00:00 EDT 1990 · Journal of the American Chemical Society; (USA)

DOI:https://doi.org/10.1021/ja00177a020· OSTI ID:6334183

Zou, Chaofeng; Wrighton, M S ^[1]

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1. 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), Vol. 112:21; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

36 MATERIALS SCIENCE
37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
FERROCENE
CHEMICAL PREPARATION
ELECTRODES
EXPERIMENTAL DATA
MEASURING METHODS
MEDIUM TEMPERATURE
SURFACE TREATMENTS
COMPLEXES
DATA
DIENES
HYDROCARBONS
INFORMATION
IRON COMPLEXES
NUMERICAL DATA
ORGANIC COMPOUNDS
POLYENES
SYNTHESIS
TRANSITION ELEMENT COMPLEXES
360601* - Other Materials- Preparation & Manufacture
400201 - Chemical & Physicochemical Properties