The Chloro-α,α-Diphenylacetones. Preparation, Proof of Structure, and Reactions with base

Stevens, Calvin L.; Sherr, Allan E.

doi:10.1021/jo50009a007

Cited by 12 publications

(2 citation statements)

References 2 publications

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“…Hydrolysis of the 1-bromo ketone (II) proceeded in an aqueous dioxane solution at 100°to give 89% of crystalline 1,1-diphenyl-l-hydroxy-2-propanone (IV). This -hydroxy ketone was identical with the hydroxy ketone recently reported in this laboratory (4) and whose structure was proven by independent synthesis.…”

supporting

confidence: 82%

THE BROMINATION OF DIPHENYLACETONE AND SUBSEQUENT SOLVOLYSIS REACTIONS¹

Stevens¹,

Lenk²

1954

J. Org. Chem.

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supporting

confidence: 82%

THE BROMINATION OF DIPHENYLACETONE AND SUBSEQUENT SOLVOLYSIS REACTIONS¹

Stevens¹,

Lenk²

1954

J. Org. Chem.

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“…3,3‐Diphenylpropionamide (11d): A mixture of AlCl 3 (0.5 g, 3.7 mmol) and 10d (0.2 g, 1.4 mmol) in benzene (3 mL) was stirred at 25 °C for 4 h and after usual workup gave 11d (0.298 g, 97%) as a white crystalline solid: M.p. 127−128 °C, ref 42a. m.p.…”

Section: Methodsmentioning

confidence: 99%

Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions

Koltunov¹,

Walspurger²,

Sommer³

2004

Eur J Org Chem

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The electrophilic reactivity of α,β‐unsaturated amides towards weak nucleophiles such as arenes and cyclohexane, initiated either with triflic acid (CF3SO3H) or with excess AlCl3, has been studied. The amides generally condense readily with aromatics in the presence of AlCl3 to give 3‐arylpropionamides and related compounds in excellent yields, while some amides also undergo selective ionic hydrogenation with cyclohexane to give saturated amides. The proposed mechanism of these reactions involves dicationic intermediates (superelectrophiles). The direct observation of a dicationic species (by low‐temperature NMR) is reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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TheFavorskiĭ Rearrangement of Haloketones

Kende¹

2011

Organic Reactions

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The Favorskii rearrangement is the skeletal rearrangement of a alpha‐halogenated ketones in the presence of certain nucleophilic bases, such as hydroxides, alkoxides, or amines to give carboxylic acid salts, esters or amides, respectively. Monohaloketones undergo the reaction to yield derivatives of saturated acids having the same number of carbon atoms. In a similar manner, suitable dihaloketiones produce unsaturated carboxylic acids. Analogous rearrangements of trihaloketones can give rise to unsaturated halo acids. The Favorskii reaction has found application for the preparation of highly branched acyclic carboxylic acids. It is a preferred route to various 1‐cycloalkanecarboxylic acids and provides a direct method for ring contraction in simple alicyclic systems and in steroids.

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The Chloro-α,α-Diphenylacetones. Preparation, Proof of Structure, and Reactions with base

Cited by 12 publications

References 2 publications

THE BROMINATION OF DIPHENYLACETONE AND SUBSEQUENT SOLVOLYSIS REACTIONS¹

THE BROMINATION OF DIPHENYLACETONE AND SUBSEQUENT SOLVOLYSIS REACTIONS¹

Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions

TheFavorskiĭ Rearrangement of Haloketones

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The Chloro-α,α-Diphenylacetones. Preparation, Proof of Structure, and Reactions with base

Cited by 12 publications

References 2 publications

THE BROMINATION OF DIPHENYLACETONE AND SUBSEQUENT SOLVOLYSIS REACTIONS1

THE BROMINATION OF DIPHENYLACETONE AND SUBSEQUENT SOLVOLYSIS REACTIONS1

Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions

TheFavorskiĭ Rearrangement of Haloketones

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Product

Resources

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THE BROMINATION OF DIPHENYLACETONE AND SUBSEQUENT SOLVOLYSIS REACTIONS¹

THE BROMINATION OF DIPHENYLACETONE AND SUBSEQUENT SOLVOLYSIS REACTIONS¹