Reaction of fluorochlorocarbene with cyclopentadiene, indene, and their alkyl derivatives by phase transfer catalysis

Volchkov, N. V.; Zabolotskikh, A. V.; Игнатенко, А. В.; Нефедов, О. М.

doi:10.1007/bf00957859

Cited by 11 publications

(2 citation statements)

References 4 publications

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“…However, there is poor regioselectivity, and the resultant mixture of 1- and 2-fluoronaphthalenes is difficult to separate. The addition reaction of fluorinated carbene, :CFX (X = F, Cl, Br), to indene, followed by base-induced rearrangement, can also lead to 2-fluoronaphthalene . However, this reaction is not practical for synthetic purposes due to the difficulty obtaining functional starting materials.…”

Section: Introductionmentioning

confidence: 99%

A Simple, Two-Step, Site-Specific Preparation of Fluorinated Naphthalene and Phenanthrene Derivatives from Fluorobromo-Substituted Alkenes

Wang

Burton

2006

J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

A Simple, Two-Step, Site-Specific Preparation of Fluorinated Naphthalene and Phenanthrene Derivatives from Fluorobromo-Substituted Alkenes

Wang

Burton

2006

J. Org. Chem.

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“…However, the isomeric products (1- and 2-fluoronaphthalenes) were formed with little regioselectivity and were difficult to separate . The addition reaction of a fluorinated carbene : CFX (X = F, Cl, Br) to indene, followed by base-induced rearrangement, has also been utilized in the preparation of 2- fluoronaphthalene . However, this method has a limitation in the preparation of functionalized 2-fluoronaphthalenes due to the inconvenient preparation of the starting material.…”

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confidence: 99%

Site-Specific Preparation of 3-Fluoro-1-substituted-naphthalenes via a Novel Base-Catalyzed Cyclization Reaction from (E)-Monofluoroenynes

Wang

Burton

2006

Org. Lett.

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Synthesis of Fulvene Vinyl Ethers by Gold Catalysis

Ahrens

Schwarz

Lustosa

et al. 2020

Chemistry A European J

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Gold-catalyzed cyclization of 1,5-diynesw ith ketones as reagents and solvent provides diversely substituted vinyl ethers under mild conditions. The regioselectivity of such gold-catalyzed cyclizations is usually controlled by the scaffold of the diyne. Herein, we report the first solvent-controlled switchingo fr egioselectivity from a6 -endo-dig-to 5endo-dig-cyclization in these transformations,p roviding fulvene derivatives. With respectt ot he functional-group toler-ance, aryl fluorides, chlorides, bromides,and ethers are tolerated. Furthermore, the mechanism and selectivity are put to scrutinyb ye xperimental studies and at hermodynamic analysis of the product. Additionally,6 -(vinyloxy)fulvenesa re a hitherto unknown class of compounds. Theirr eactivity is briefly evaluated, to give insights into their potential applications.[ + + ] Crystallographic investigation;T heoreticali nvestigation Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Reaction of fluorochlorocarbene with cyclopentadiene, indene, and their alkyl derivatives by phase transfer catalysis

Cited by 11 publications

References 4 publications

A Simple, Two-Step, Site-Specific Preparation of Fluorinated Naphthalene and Phenanthrene Derivatives from Fluorobromo-Substituted Alkenes

A Simple, Two-Step, Site-Specific Preparation of Fluorinated Naphthalene and Phenanthrene Derivatives from Fluorobromo-Substituted Alkenes

Site-Specific Preparation of 3-Fluoro-1-substituted-naphthalenes via a Novel Base-Catalyzed Cyclization Reaction from (E)-Monofluoroenynes

Synthesis of Fulvene Vinyl Ethers by Gold Catalysis

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