The Friedel—Crafts Reaction with Disubstituted Ethylene Oxides. III. The Rearrangement of α,α-Dimethylbibenzyl

Somerville, Willard T.; Spoerri, Paul E.

doi:10.1021/ja01135a026

Cited by 5 publications

(1 citation statement)

References 2 publications

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“…Isomerization of l,2-diphenyl-2-methylpropane and of (¿/-2,3-diphenylbutane to meso-2,3-diphenylbutane by aluminum chloride at room temperature has been described. 10 When we repeated the preparation of this diphenylbutane by the two methods used by these workers (both of which involved aluminum chloride), we found the products to consist of four isomers. Somerville and Spoerri recognized the presence of meso-2,3-diphenylbutane in their products and separated it by chilling the mixture and filtering off the crystalline isomer.…”

Section: Resultsmentioning

confidence: 96%

Alkylbenzenes. XIV. Diphenylalkanes as Intermediates in Fragmentation, Rearrangement, and Disproportionation Reactions of Alkylbenzenes

Roberts¹,

Khalaf²,

Greene³

1964

J. Am. Chem. Soc.

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Section: Resultsmentioning

confidence: 96%

Alkylbenzenes. XIV. Diphenylalkanes as Intermediates in Fragmentation, Rearrangement, and Disproportionation Reactions of Alkylbenzenes

Roberts¹,

Khalaf²,

Greene³

1964

J. Am. Chem. Soc.

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Ethylene Oxides

Rosowsky¹

1964

Chemistry of Heterocyclic Compounds: A Series of Monographs

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A Modular Dual‐Catalytic Aryl‐Chlorination of Alkenes

Li,

Bunescu,

Drazen

et al. 2024

Angewandte Chemie

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Alkyl chlorides are a class of versatile building blocks widely used to generate C(sp3)‐rich scaffolds through transformation such as nucleophilic substitution, radical addition reactions and metal‐catalyzed cross‐coupling processes. Despite their utility in the synthesis of high‐value functional molecules, distinct methods for the preparation of alkyl chlorides are underrepresented. Here, we report a visible‐light‐mediated dual catalysis strategy for the modular synthesis of highly functionalized and structurally diverse arylated chloroalkanes via the coupling of diaryliodonium salts, alkenes and potassium chloride. A distinctive aspect of this transformation is a ligand‐design‐driven approach for the development of a copper(II)‐based atom‐transfer catalyst that enables the aryl‐chlorination of electron‐poor alkenes, complementing its iron(III)‐based counterpart that accommodates non‐activated aliphatic alkenes and styrene derivatives. The complementarity of the two dual catalytic systems allows the efficient aryl‐chlorination of alkenes bearing different stereo‐electronic properties and a broad range of functional groups, maximizing the structural diversity of the 1‐aryl, 2‐chloroalkane products.

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The Friedel—Crafts Reaction with Disubstituted Ethylene Oxides. III. The Rearrangement of α,α-Dimethylbibenzyl

Cited by 5 publications

References 2 publications

Alkylbenzenes. XIV. Diphenylalkanes as Intermediates in Fragmentation, Rearrangement, and Disproportionation Reactions of Alkylbenzenes

Alkylbenzenes. XIV. Diphenylalkanes as Intermediates in Fragmentation, Rearrangement, and Disproportionation Reactions of Alkylbenzenes

Ethylene Oxides

A Modular Dual‐Catalytic Aryl‐Chlorination of Alkenes

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