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2,2,5,5 Tetramethyltetrahydrofuran

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2,2,5,5-Tetramethyltetrahydrofuran

In chemistry, 2,2,5,5-tetramethyltetrahydrofuran or 2,2,5,5-tetramethyloxolane is a heterocyclic compound with the formula C
8
H
16
O
, or (CH3)2(C(CH2)2OC)(CH3)2. It can be seen as derivative of tetrahydrofuran (oxolane) with two methyl groups replacing two hydrogen atoms on each of the carbon atoms in the ring that are adjacent to the oxygen. It can be seen also as a cyclic ether of 2,5-dimethylhexane, an isomer of octane. It is sometimes denoted by the abbreviations TMTHF or Me4THF.

Contents

The compound is sometimes used as a polar aprotic solvent in research chemistry and as a reagent in chemical synthesis.

Natural occurrence

The compound is produced in small quantities by the mycelium of Tuber borchii, a mushroom similar to the truffle.

Synthesis and chemistry

The compound can be prepared by treating 2,5-dimethylhexane-2,5-diol with sulfuric acid.

TMTHF reacts with benzene in the presence of triflic acid to form 1,1,4,4-dimethyltetralin and symmetric tetramethyloctahydroanthracene. This and other similar reactions can be used for the selective preparation of derivatives of naphthalene, anthracene, and tetracene, and other fused-ring aromatic hydrocarbons.

TMTHF undergoes photolysis by UV; in aqueous solution, the products are mainly methane, ethane, and 2-hydroxy-2,5,5-trimethyltetrahydrofuran. The dehydration of TMTHF yields alkenes like 2,5-dimethyl-2,4-hexadiene and 2,5-dimethyl-1,5-hexadiene.

Reaction with fluorine substitutes it for all hydrogen atoms to yield perfluoro(2,2,5,5-tetramethyltetrahydrofuran) C
8
F
16
O
(bp 99 C, mp -31 C).

References

2,2,5,5-Tetramethyltetrahydrofuran Wikipedia


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