Organic Chemistry of Ferrocene. II. The Preparation of Ferrocenyl Aliphatic

Rinehart, Kenneth J.; Curby, Ronald J.; Sokol, Phillip E.

doi:10.1021/ja01570a028

J. Am. Chem. Soc.

1957

DOI: 10.1021/ja01570a028

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Organic Chemistry of Ferrocene. II. The Preparation of Ferrocenyl Aliphatic

Kenneth J. Rinehart¹,

Ronald J. Curby²,

Phillip E. Sokol³

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Cited by 117 publications

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The Synthesis of Substituted Ferrocenes and other π‐Cyclopentadienyl‐Transition Metal Compounds

Bublitz

Rinehart

2011

Organic Reactions

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The discovery of dicyclopentadienyliron (ferrocene) in 1951 led to the development of an entirely new area of organometallic chemistry that of the pi‐metallohydrocarbons. Representative compounds are the pi‐metalloarenes such as dibenzenechromium, the pi‐methallopseudoarenes such as ferrocene, and the pi‐metalloolefin complexes such as butadiene iron tricarbonyl Since there is a great amount of literature available at this time, the treatment here is limited to three dimensions: to include only compounds containing cyclopentadienyl rings, of these to include only those which have shown to undergo aromatic substitution,reactions and within this group only synthetic aspects of their chemistry. This nearly restricts the discussion to syntheses of substituted ferrocenes.

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The Synthesis of Substituted Ferrocenes and other π‐Cyclopentadienyl‐Transition Metal Compounds

Bublitz

Rinehart

2011

Organic Reactions

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Cyclopentadienyl and Arene Metal Compounds

Wilkinson

Cotton

1959

Progress in Inorganic Chemistry

104

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Willgerodt‐Kindler Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The preparation of thionamide from the reaction of an organic molecule (from acetophenone and anhydrous primary or secondary amines) with sulfur and amine is generally called the Willgerodt–Kindler reaction. Occasionally, this reaction is also termed as the Willgerodt–Kindler redox amidation. The resulting thionamides are further converted into carbonamides by hot aqueous ammonia under the Willgerodt condition. The high boiling point of morpholine, an intrinsic feature, allows the Willgerodt–Kindler reaction to take place in an open vessel instead of an autoclave or a sealed tube. For comparison, under the condition of Willgerodt reaction, it has been found that the presence of pyridine is beneficial to the reaction by lowering the reaction temperature from 210°C to 165°C and raising the yield of phenylacetamide from 49% to 64%. It has been reported that the ketones with a straight chain usually give much better yields of amides than the branched ketones with the same number of carbon atoms at the main chains under comparable reaction conditions. Furthermore, the yields of amide from ketones decrease inversely with the increase of chain length of the alkyl groups. Moreover, the amount of sulfur has also been found to be critical. This reaction has very broad application in the preparation of thionamides and carboxylic acids.

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Organic Chemistry of Ferrocene. II. The Preparation of Ferrocenyl Aliphatic

Cited by 117 publications

References 0 publications

The Synthesis of Substituted Ferrocenes and other π‐Cyclopentadienyl‐Transition Metal Compounds

The Synthesis of Substituted Ferrocenes and other π‐Cyclopentadienyl‐Transition Metal Compounds

Cyclopentadienyl and Arene Metal Compounds

Willgerodt‐Kindler Reaction

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