ChemInform Abstract: Photodimerization of Bromo Derivatives of Furfural.

Tymyanskii, Ya. R.; Feigel'man, V. M.; Zubkov, Oleg A.; Novikov, V. N.; Knyazhanskii, M. I.; Pustovarov, V. S.

doi:10.1002/chin.198824177

Search citation statements

Order By: Relevance

Paper Sections

Select...

Introduction1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2002

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This compound had previously been obtained either through an Ullmann condensation utilising 5-iodo-2-furfural, [1] Pd-catalysed coupling of 2-furfural 1, [2] or via the photolytic dimerisation of 5-bromo-2-furfural 2. [3] The photolytic substitution of 3-and 5-halogenated-2-furyl derivatives in aromatic solvents was reported to give good yields of the corresponding 3-and 5-aryl derivatives. [4] However, reports on the photochemical aryl coupling reactions of 5-bromo-2-furfural 2 with other derivatives are limited.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5,5′-Diformyl-2,2′-difuran from 2-Furfural by Photochemical Aryl Coupling

Taljaard¹,

Burger

2002

Advanced Synthesis & Catalysis

View full text Add to dashboard Cite

The synthesis of 5,5′‐diformyl‐2,2′‐difuran (IUPAC name: [2,2′‐bifuryl]‐5,5′‐dicarbaldehyde) in good yields by the intermolecular coupling of 2‐furfural and 5‐bromo‐2‐furfural has been achieved. Optimum yields were obtained when mixtures of the substrates in acetonitrile were treated with polyvinylpyridine powder (Reillex 402), and irradiated with UV light through a quartz filter. Low yields of coupling product were obtained in the absence of this base or if hydrocarbon solvents were used. A mechanistic pathway involving a transient exciplex intermediate has been proposed.

show abstract

Section: Introductionmentioning

confidence: 99%