2,3-Dihydrofuran

2,3-Dihydrofuran
Names
	Preferred IUPAC name 2,3-Dihydrofuran
Identifiers
CAS Number	1191-99-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:51662 ;
ChemSpider	64096 ;
ECHA InfoCard	100.013.407
PubChem CID	70934;
UNII	07M2EY3BG1 ;
CompTox Dashboard (EPA)	DTXSID9061594 ;
	InChI InChI=1S/C4H6O/c1-2-4-5-3-1/h1,3H,2,4H2 Key: JKTCBAGSMQIFNL-UHFFFAOYSA-N ; InChI=1/C4H6O/c1-2-4-5-3-1/h1,3H,2,4H2 Key: JKTCBAGSMQIFNL-UHFFFAOYAF;
	SMILES O1\C=C/CC1;
Properties
Chemical formula	C4H6O
Molar mass	70.091 g·mol−1
Density	0,927 g/mL
Boiling point	54.6 °C (130.3 °F; 327.8 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). verify (what is ?) Infobox references

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

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

Synthesis and occurrence

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

^ 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.
^ 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.
^ Tschantz, M. A.; Burgess, L. E.; Meyers, A. I. (1996). "4-Ketoundecanoic Acid". Organic Syntheses. 73: 215. doi:10.15227/orgsyn.073.0215.
^ Gilchrist, Thomas L. (1997). Heterocyclic Chemistry (3rd ed.). Liverpool: Longman. pp. 209–212.
^ 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.
^ 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.
^ 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.
^ 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.

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[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.

[Gil-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.

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