Dibenzofuran. XII. Metalation of Some Bromo Derivatives

Gilman, Henry; Willis, H. B.; Swislowsky, Jack.

doi:10.1021/ja01875a014

Cited by 14 publications

(2 citation statements)

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“…This reaction is unusual because the halogen is meta to the activating linkage. The tendency for the electron-attracting group to occupy a position where it will be better able to neutralize the electron-donating group is shown, however, by the fact that, after carbonation, the products are found to be 3and 4-carboxydibenzofurans (47).…”

Section: Metal-halogen Interchange and Related Effectsmentioning

confidence: 99%

The Chemical Behavior of the Organoalkali Compounds.

Morton¹

1944

Chem. Rev.

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Section: Metal-halogen Interchange and Related Effectsmentioning

confidence: 99%

The Chemical Behavior of the Organoalkali Compounds.

Morton¹

1944

Chem. Rev.

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“…The first aryne ever proposed was the 2,3-benzofuranyne; however, this structural assignment was later called into question . Subsequent contributions in the area of oxacyclic arynes are limited to scattered examples involving dehydrohalogenation of benzofuran derivatives and access to the 6,7-benzofuranyne using butyllithium reagents . With regard to oxacyclohexynes, even less is known, with only two studies involving metalated oxacyclohexynes in the literature .…”

Section: Introductionmentioning

confidence: 99%

Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes

2016

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We report synthetic methodology that permits access to two oxacyclic strained intermediates, the 4,5-benzofuranyne and the 3,4-oxacyclohexyne. In situ trapping of these intermediates affords an array of heterocyclic scaffolds by the formation of one or more new C-C or C-heteroatom bonds. Experimentally determined regioselectivities were consistent with predictions made using the distortion/interaction model and were also found to be greater compared to selectivities seen in the case of trapping experiments of the corresponding N-containing intermediates. These studies demonstrate the synthetic versatility of oxacyclic arynes and alkynes for the synthesis of functionalized heterocycles, while further expanding the scope of the distortion/interaction model. Moreover, these efforts underscore the value of harnessing strained heterocyclic intermediates as a unique approach to building polycyclic heteroatom-containing frameworks.

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The Halogen‐Metal Interconversion Reaction with Organolithium Compounds

Jones

Gilman

2011

Organic Reactions

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The reaction of an organic halide with an organometallic compound in which the metal and the halogen atoms exchange laces is known as the halogen‐metal interconversion reaction. Numerous studies have established the fact that the halogen‐lithium interconversion is a general and widely applicable reaction. Many organic halides do not react satisfactorily with metallic lithium to form RLi compounds or with metallic magnesium to form Grignard reagents. However, the desired organolithium compound often can be obtained by a halogen‐metal Interconversion reaction. The halogen‐metal interconversion greatly extends the utility of organolithium and Grignard‐type reactions.

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Dibenzofuran. XII. Metalation of Some Bromo Derivatives

Cited by 14 publications

References 0 publications

The Chemical Behavior of the Organoalkali Compounds.

The Chemical Behavior of the Organoalkali Compounds.

Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes

The Halogen‐Metal Interconversion Reaction with Organolithium Compounds

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