Publication

Fluoronaphthalene building blocks via arynes: A solution to the problem of positional selectivity

Eric Masson
2005
Journal Articles

Abstract

When 3-fluoro- and 3-chloro-1,2-didehydrobenzenes are generated in the presence of 2-(trimethylsilyl)furan, two regioisomeric cycloadducts are formed in a 1:2 ratio. However, regioselectivity can be installed by fitting one bulky trimethylsilyl group into sterically crit. positions of each of the two reaction components. Thus 3-fluoro-6-trimethylsilyl-1,2-didehydrobenzene and 2-(trimethylsilyl)furan give one cycloadduct exclusively. In this way, the Diels-Alder reaction between suitably adorned arynes and similarly designed furans can open an entry to naphthalene derivs. that have unprecedented substituent patterns that qualify them as building blocks for pharmaceutical or agricultural research. The acid-catalyzed isomerization of model 1,4-epoxy-1,4-dihydronaphthalenes, the aryne/furan cycloadducts, exhibits unexpected effects on rates and regioselectivity. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/3b0cf35a-c88e-4b0c-8be4-4b689e68fc26

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Eric Masson
2005
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3b0cf35a-c88e-4b0c-8be4-4b689e68fc26

About this result

Related concepts (16)

Furan

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans. Furan is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. It is soluble in common organic solvents, including alcohol, ether, and acetone, and is slightly soluble in water. Its odor is "strong, ethereal; chloroform-like". It is toxic and may be carcinogenic in humans.

1,3-Dipolar cycloaddition

The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic application were established in the 1960s, primarily through the work of Rolf Huisgen. Hence, the reaction is sometimes referred to as the Huisgen cycloaddition (this term is often used to specifically describe the 1,3-dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-triazole).

Pharmaceutical marketing

Many countries have measures in place to limit advertising by pharmaceutical companies. Pharmaceutical company spending on marketing generally exceeds that of its research budget. In Canada,

1.7 billion was spent in 2004 to market drugs to physicians; in the United States,

21 billion was spent in 2002. In 2005, money spent on pharmaceutical marketing in the United States was estimated at

29.9 billion with one estimate as high as

57 billion. When the U.S.

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