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2,3-Dihydrofuran
Skeletal formula of 2,3-dihydrofuran
Ball-and-stick model of the 2,3-dihydrofuran molecule
Names
Preferred IUPAC name
2,3-Dihydrofuran
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.407 Edit this at Wikidata
UNII
  • InChI=1S/C4H6O/c1-2-4-5-3-1/h1,3H,2,4H2 checkY
    Key: JKTCBAGSMQIFNL-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O/c1-2-4-5-3-1/h1,3H,2,4H2
    Key: JKTCBAGSMQIFNL-UHFFFAOYAF
  • O1\C=C/CC1
Properties
C4H6O
Molar mass 70.091 g·mol−1
Density 0,927 g/mL
Boiling point 54.6 °C (130.3 °F; 327.8 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

2,3-Dihydrofuran is a heterocyclic compound with the formula C4H6O. It is isomeric with 2,5-dihydrofuran. 2,3-Dihydrofuran is one of the simplest enol ethers. It is a colorless volatile liquid.

Reactions[edit]

It undergoes lithiation upon treatment with butyl lithium. The resulting 2-lithio derivative is a versatile intermediate.[2][3]

Synthesis and occurrence[edit]

2,3-Dihydrofurans are intermediates in the Feist–Benary synthesis of furans from α-halogen ketones and β-dicarbonyl compounds.[4]

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.[5][6] Iodine can also serve as a catalyst[7] as well as Raney nickel.[8]

References[edit]

  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. 69 (12): 3002–3004. doi:10.1021/ja01204a020.
  2. ^ Krzysztof Jarowicki; Philip J. Kocienski; Liu Qun (2002). "1,2-Metallate Rearrangement: (Z)-4-(2-Propenyl)-3-octen-1-ol". Org. Synth. 79: 11. doi:10.15227/orgsyn.079.0011.
  3. ^ Tschantz, M. A.; Burgess, L. E.; Meyers, A. I. (1996). "4-Ketoundecanoic Acid". Organic Syntheses. 73: 215. doi:10.15227/orgsyn.073.0215.
  4. ^ Gilchrist, Thomas L. (1997). Heterocyclic Chemistry (3rd ed.). Liverpool: Longman. pp. 209–212.
  5. ^ Kim N. Tu; Chao Gao; Suzanne A. Blum (2018). "An Oxyboration Route to a Single Regioisomer of Borylated Dihydrofurans and Isochromenes". J. Org. Chem. 83: 11204. doi:10.1021/acs.joc.8b01790.
  6. ^ Hao Liu; Zhenliang Sun; Kai Xu; Yan Zheng; Delong Liu; Wanbin Zhang (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. 22: 4680. doi:10.1021/acs.orglett.0c01483.
  7. ^ Domenic P. Pace; Raphaël Robidas; Uyen P. N. Tran; Claude Y. Legault; Thanh Vinh Nguyen (2021). "Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights". J. Org. Chem. 86: 8154. doi:10.1021/acs.joc.1c00608.
  8. ^ Evgeny V. Pospelov; Alexander V. Zhirov; Baglan Kamidolla; Alexey Yu. Sukhorukov (2023). "Reductive Denitrogenation of Six-membered Cyclic Nitronates to Densely Substituted Dihydrofurans with Raney® Nickel/AcOH System". Adv. Synth. Catal. 365: 8154. doi:10.1002/adsc.202300573.


source: https://en.wikipedia.org/wiki/2,3-Dihydrofuran

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