Many-membered carbon rings. XXV. Derivatives of 3,3,8,8-tetramethyl[10]paracyclophane

Blomquist, A. T.; Smith, Brandes H.

doi:10.1021/jo01280a118

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Clemmensen Reduction of Ketones in Anhydrous Organic Solvents

Vedejs

2011

Organic Reactions

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The Clemmensen reduction of ketones and aldehydes using zinc and hydrochloric acid is the simplest direct method for converting the carbonyl group into a methylene group. Typically the carbonyl is refluxed for several hours with 40% hydrochloric acid, amalgamated zinc, and a water‐immiscible organic solvent such as tolurene. Because of these harsh conditions, reports of successful Clemmensen reduction of polyfunctional ketones have been rare. A milder procedure using dry hydrogen chloride in organic solvent extends the potential of this reaction. Other developments that define scope of both aqueous and anhydrous reduction conditions are discussed and an effort is made to compare the properties of possible reduction intermediates with other organozinc species.

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Clemmensen Reduction of Ketones in Anhydrous Organic Solvents

Vedejs

2011

Organic Reactions

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The Acyloin Condensation

2011

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The acyloin condensation usually involves the reductive dimerization of a carboxylic ester, although acid chlorides and the anhydrides have been used. The reducing agent is in an alkali metal and the product is an ene‐diolate. Two gram‐atoms of metal are required for each mole of ester with the concomitant formation of a mole of akoxide and one‐half mole of the ene‐diolate. Oxidation of acyloins to diketoes can be accomplished by a variety of reagents. Acyloins can be reduced to ketones by various modifications of the Clemmenson technique. Under mild conditions the ketone will dominate. This chapter presents a complete picture of both the linear and cyclic acyloin condensation with particular emphasis on developments since 1960. The discussion is closely limited to the acyloin condensation and its modifications.

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Resolving Agents and Resolutions in Organic Chemistry

Wilen

1971

Topics in Stereochemistry

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Many-membered carbon rings. XXV. Derivatives of 3,3,8,8-tetramethyl[10]paracyclophane

Cited by 4 publications

References 3 publications

Clemmensen Reduction of Ketones in Anhydrous Organic Solvents

Clemmensen Reduction of Ketones in Anhydrous Organic Solvents

The Acyloin Condensation

Resolving Agents and Resolutions in Organic Chemistry

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