2,3-Dihydrofuran

Reactions

It undergoes lithiation upon treatment with butyl lithium. The resulting 2-lithio derivative is a versatile intermediate.

Synthesis and occurrence

2,3-Dihydrofurans are intermediates in the Feist–Benary synthesis of furans from α-halogen ketones and β-dicarbonyl compounds.

The 2,3-dihydrofuran ring can be synthesized by several methods. These routes usually involve cyclization or cycloaddition reactions of carbonyl compounds using metal-containing catalysts. Iodine can also serve as a catalyst as well as Raney nickel.

References

References

1. Wilson, Christopher L.. (December 1947). "Reactions of Furan Compounds. VII. Thermal Interconversion of 2,3-Dihydrofuran and Cyclopropane Aldehyde". Journal of the American Chemical Society.
2. (2002). "1,2-Metallate Rearrangement: (Z)-4-(2-Propenyl)-3-octen-1-ol". Org. Synth..
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4. (1997). "Heterocyclic Chemistry". Longman.
5. (2018). "An Oxyboration Route to a Single Regioisomer of Borylated Dihydrofurans and Isochromenes". J. Org. Chem..
6. (2020). "Pd-Catalyzed Asymmetric Allylic Substitution Cascade of But-2-ene-1,4-diyl Dimethyl Dicarbonate for the Synthesis of Chiral 2,3-Dihydrofurans". Org. Lett..
7. (2021). "Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights". J. Org. Chem..
8. (2023). "Reductive Denitrogenation of Six-membered Cyclic Nitronates to Densely Substituted Dihydrofurans with Raney® Nickel/AcOH System". Adv. Synth. Catal..