Publication

1-Ethoxy-3-trifluoromethyl-1,3-butadiene and congeners as Diels-Alder components opening an entry to functionalized (trifluoromethyl)benzenes and -pyridines

Manfred Schlosser
2002
Journal Articles

Abstract

1-Ethoxy-3-trifluoromethyl-1,3-butadiene and its 2-bromo- and 2-phenyl-substituted derivs. have been prepd. by Wittig methylenation of the corresponding 4-ethoxy-1,1,1-trifluoro-3-buten-2-ones, which in turn are readily accessible from trifluoroacetic acid. The electron-rich/electron-poor dienes combine smoothly with di-Me acetylenedicarboxylate and Me propiolate to provide trifluoromethyl-substituted phthalates or benzoates. Satisfactory yields of 4-(trifluoromethyl)pyridinecarboxylic acids can even be achieved with Me cyanoformate, a less reactive dienophile, if a large excess of the dienophile is employed. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/ff436c9b-9c0b-4343-a25c-0e1e94b18849

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Manfred Schlosser
2002
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/ff436c9b-9c0b-4343-a25c-0e1e94b18849

About this result

Related concepts (5)

Diels–Alder reaction

In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a pericyclic reaction with a concerted mechanism. More specifically, it is classified as a thermally-allowed [4+2] cycloaddition with Woodward–Hoffmann symbol [π4s + π2s]. It was first described by Otto Diels and Kurt Alder in 1928.

Polycyclic aromatic hydrocarbon

A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. PAHs are uncharged, non-polar and planar. Many are colorless. Many of them are found in coal and in oil deposits, and are also produced by the incomplete combustion of organic matter—for example, in engines and incinerators or when biomass burns in forest fires.

Dicyclopentadiene

Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula . At room temperature, it is a white brittle wax, although lower purity samples can be straw coloured liquids. The pure material smells somewhat of soy wax or camphor, with less pure samples possessing a stronger acrid odor. Its energy density is 10,975 Wh/l. Dicyclopentadiene is a co-produced in large quantities in the steam cracking of naphtha and gas oils to ethylene. The major use is in resins, particularly, unsaturated polyester resins.