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Ferrocenecarboxaldehyde
Ferrocenecarboxaldehyde is the organoiron compound with the formula . The molecule consists of ferrocene substituted by an formyl group on one of the cyclopentadienyl rings. It is an orange, air-stable solid that is soluble in organic solvents. Synthesis Ferrocenecarboxaldehyde is prepared by Vilsmeier-Haack reaction (formylation) using dimethylformamide and phosphorus oxychloride. Diformylation does not occur readily. According to X-ray crystallography ferrocenecarboxaldehyde adopts the expected sandwich structure exhibited by other ferrocenes. The formyl group is coplanar with its attached ring. In its IR spectrum, ferrocenecarboxaldehyde is characterized by a low frequency νCO band at 1670 cm−1 vs 1704 cm−1 for benzaldehyde. Reactions Ferrocenecarboxaldehyde behaves like other aldehydes in terms of its reactivity, the main difference is that it is electroactive. Its basicity is indicated by the solubility of the compound in hydrochloric acid. Ferrocenecar ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Vinylferrocene
Vinylferrocene is the organometallic compound with the formula (C5H5)Fe(C5H4CH=CH2). It is a derivative of ferrocene, with a vinyl group attached to one cyclopentadienyl ligand. As the ferrocene analogue of styrene, it is the precursor to some polyferrocenes. It is an orange, air-stable oily solid that is soluble in nonpolar organic solvents. Vinylferrocene can be prepared by the dehydration of α-hydroxylethylferrocene, which is obtained from acetylferrocene. It can also be made by a Wittig reaction of ferrocenecarboxaldehyde Ferrocenecarboxaldehyde is the organoiron compound with the formula . The molecule consists of ferrocene substituted by an formyl group on one of the cyclopentadienyl rings. It is an orange, air-stable solid that is soluble in organic solvents. ....{{cite journal , vauthors = Liu WY, Xu QH, Ma YX, Liang YM, Dong NL, Guan DP , journal= J. Organomet. Chem., year=2001, volume=625, pages=128–132, doi=10.1016/S0022-328X(00)00927-X, title=Solvent-free s ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ferrocene
Ferrocene is an organometallic chemistry, organometallic compound with the formula . The molecule is a Cyclopentadienyl complex, complex consisting of two Cyclopentadienyl anion, cyclopentadienyl rings sandwiching a central iron atom. It is an orange solid with a camphor-like odor that Sublimation (phase transition), sublimes above room temperature, and is soluble in most organic solvents. It is remarkable for its stability: it is unaffected by air, water, strong bases, and can be heated to 400 °C without decomposition. In oxidizing conditions it can reversibly react with strong acids to form the ferrocenium cation . Ferrocene and the ferrocenium cation are sometimes abbreviated as Fc and respectively. The first reported synthesis of ferrocene was in 1951. Its unusual stability puzzled chemists, and required the development of new theory to explain its formation and bonding. The discovery of ferrocene and its many Structural analog, analogues, known as metallocenes, sparke ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organoiron Compound
Organoiron chemistry is the chemistry of iron compounds containing a carbon-to-iron chemical bond. Organoiron compounds are relevant in organic synthesis as reagents such as iron pentacarbonyl, diiron nonacarbonyl and disodium tetracarbonylferrate. Although iron is generally less active in many catalytic applications, it is less expensive and " greener" than other metals. Organoiron compounds feature a wide range of ligands that support the Fe-C bond; as with other organometals, these supporting ligands prominently include phosphines, carbon monoxide, and cyclopentadienyl, but hard ligands such as amines are employed as well. Iron(–II) and Iron(0) Carbonyl complexes Important iron carbonyls are the three neutral binary carbonyls, iron pentacarbonyl, diiron nonacarbonyl, and triiron dodecacarbonyl. One or more carbonyl ligands in these compounds can be replaced by a variety of other ligands including alkenes and phosphines. An iron(–II) complex, disodium tetracarbonylfe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetylferrocene
Acetylferrocene is the organoiron compound with the formula (C5H5)Fe(C5H4COCH3). It consists of ferrocene substituted by an acetyl group on one of the cyclopentadienyl rings. It is an orange, air-stable solid that is soluble in organic solvents. Preparation and reactions Acetylferrocene is prepared by Friedel-Crafts acylation of ferrocene, usually with acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ... (Ac2O): :Fe(C5H5)2 + Ac2O → (C5H5)Fe(C5H4Ac) + HOAc The experiment is often conducted in the instructional laboratory to illustrate acylation as well as chromatographic separations. Acetylferrocene can be converted to many derivatives, e.g., reduction to the chiral alcohol (C5H5)Fe(C5H4CH(OH)Me) and precursor to vinylferrocene. The oxidized derivativ ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ferrocenecarboxylic Acid
Ferrocenecarboxylic acid is the organoiron compound with the formula . It is the simplest carboxylic acid derivative of ferrocene. It can be prepared in two steps from ferrocene by acylation with a 2-chlorobenzoyl chloride followed by hydrolysis. Reactions and derivatives The pKa of ferrocenecarboxylic acid is 7.8. The acidity increases more than a thousand-fold, to pH 4.54 upon oxidation to the ferrocenium cation. By treatment with thionyl chloride, the carboxylic acid anhydride () is produced. Derivatives of ferrocenecarboxylic acid are components of some redox switches. Related compounds * 1,1'-Ferrocenedicarboxylic acid 1,1'-Ferrocenedicarboxylic acid is the organoiron compound with the formula . It is the simplest dicarboxylic acid derivative of ferrocene. It is a yellow solid that is soluble in aqueous base. The 1,1' part of its name refers to the location o ... * Ferrocenecarboxaldehyde References {{Reflist Ferrocenes Cyclopentadienyl complexes Aromatic ac ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Directed Ortho Metalation
Directed ortho metalation (DoM) is an adaptation of electrophilic aromatic substitution in which electrophiles attach themselves exclusively to the ortho- position of a direct metalation group or DMG through the intermediary of an aryllithium compound. The DMG interacts with lithium through a hetero atom. Examples of DMG's are the methoxy group, a tertiary amine group and an amide group. The compound can be produced by directed lithiation of anisole. The general principle is outlined in ''scheme 1''. An aromatic ring system with a DMG group 1 interacts with an alkyllithium such as ''n''-butyllithium in its specific aggregation state (hence (R-Li)n) to intermediate 2 since the hetero atom on the DMG is a Lewis base and lithium the Lewis acid. The very basic alkyllithium then deprotonates the ring in the nearest ortho- position forming the aryllithium 3 all the while maintaining the acid-base interaction. An electrophile reacts in the next phase in an electrophilic aromati ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Azomethine
In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure ( = alkyl or aryl, but not hydrogen). They can be considered a sub-class of imines, being either secondary ketimines or secondary aldimines depending on their structure. Anil refers to a common subset of Schiff bases: imines derived from anilines. The term can be synonymous with azomethine which refers specifically to secondary aldimines (i.e. where R' ≠ H). Synthesis Schiff bases can be synthesized from an aliphatic or aromatic amine and a carbonyl compound by nucleophilic addition forming a hemiaminal, followed by a dehydration to generate an imine. In a typical reaction, 4,4'-oxydianiline reacts with ''o''-vanillin: Schiff bases can also be synthesized via the Aza-Wittig reaction. Biochemistry Schiff bases have been investigated in relation to a wide range of contexts, including antimicrobial, antiviral and anticancer activity. They have also been considered ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Imine
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions. Distinction is sometimes made between aldimines and ketimines, derived from aldehydes and ketones, respectively. Structure In imines the five core atoms (C2C=NX, ketimine; and C(H)C=NX, aldimine; X = H or C) are coplanar. Planarity results from the sp2-hybridization of the mutually double-bonded carbon and the nitrogen atoms. The C=N distance is 1.29–1.31 Å for nonconjugated imines and 1.35 Å for conjugated imines. By contrast, C−N distances in amines and nitriles are 1.47 and 1.16 Å respectively. Rotation about the C=N bond is slow. Using NMR spectroscopy, both E–Z notation, ''E'' and ''Z'' isomers of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Journal Of Organometallic Chemistry
The ''Journal of Organometallic Chemistry'' is a peer-reviewed scientific journal published by Elsevier, covering research on organometallic chemistry. According to the ''Journal Citation Reports'', the journal has a 2021 impact factor The impact factor (IF) or journal impact factor (JIF) of an academic journal is a type of journal ranking. Journals with higher impact factor values are considered more prestigious or important within their field. The Impact Factor of a journa ... of 2.345. References External links * Organic chemistry journals Elsevier academic journals Academic journals established in 1964 English-language journals Monthly journals {{chem-journal-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
