Diels–Alder Reaction of Thiophene: Dramatic Effects of High‐Pressure/Solvent‐Free Conditions | Zendy

Kumamoto Koji | Zendy; Fukada Isao | Zendy; Kotsuki Hiyoshizo | Zendy

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Diels–Alder Reaction of Thiophene: Dramatic Effects of High‐Pressure/Solvent‐Free Conditions

Author(s) -

Kumamoto Koji,

Fukada Isao,

Kotsuki Hiyoshizo

Publication year - 2004

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200353487

Subject(s) - maleimide , thiophene , maleic anhydride , diels–alder reaction , adduct , solvent , chemistry , yield (engineering) , polymer chemistry , high pressure , organic chemistry , materials science , polymer , catalysis , thermodynamics , copolymer , metallurgy , physics

The extraordinary power of high‐pressure/solvent‐free conditions for the Diels–Alder reaction of thiophene has been established. For example, maleic anhydride (X=O) reacted with thiophene at 0.8 GPa and 100 °C to give the desired exo adduct in almost quantitative yield (see scheme). Further application of this method to maleimide (X=NR) and acrylic dienophiles demonstrated its remarkable potential.

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