2,3-Dihydrofuran is a

heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

with the formula . It is

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

ic with

2,5-dihydrofuran 2,5-Dihydrofuran is an organic compound classified as a monounsaturated derivative of furan Furan is a Heterocyclic compound, heterocyclic organic compound, consisting of a five-membered aromatic Ring (chemistry), ring with four carbon Atom, ...

. 2,3-Dihydrofuran is one of the simplest

enol ether In organic chemistry an enol ether is an alkene with an alkoxy substituent. The general structure is R2C=CR-OR where R = H, alkyl or aryl. A common subfamily of enol ethers are vinyl ethers, with the formula ROCH=CH2. Important enol ethers incl ...

s. It is a colorless volatile liquid.

Reactions

It undergoes lithiation upon treatment with

butyl lithium Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis: * ''n''-Butyllithium, abbreviated BuLi or nBuLi * ''sec''-Butyllithium, abbreviated ''sec''-BuLi or sBuLi, has 2 stereoisomers, ...

. The resulting 2-lithio derivative is a versatile intermediate.

Synthesis and occurrence

2,3-Dihydrofurans are intermediates in the

Feist–Benary synthesis The Feist–Benary synthesis is an organic reaction between α-Halo ketone, α-halo ketones and β-carbonyl, dicarbonyl compounds to produce substituted furan compounds. This condensation reaction is catalysis, catalyzed by amines such as ammonia ...

of furans from α-

halogen The halogens () are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and the radioactive elements astatine (At) and tennessine (Ts), though some authors would ...

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

s and β-

dicarbonyl In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls ...

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 Raney nickel , also called spongy nickel, is a fine-grained solid composed mostly of nickel derived from a nickel–aluminium alloy. Several grades are known, of which most are gray solids. Some are pyrophoric, but most are used as air-stable s ...

References

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