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3,3,4,4-Tetramethyltetrahydrofuran

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3,3,4,4-Tetramethyltetrahydrofuran
Names
Preferred IUPAC name
3,3,4,4-Tetramethyloxolane
Other names
Tetrahydro-3,3,4,4-tetramethylfuran
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C8H16O/c1-7(2)5-9-6-8(7,3)4/h5-6H2,1-4H3
    Key: DAQZHQHZMPVCQW-UHFFFAOYSA-N
  • CC1(C)COCC1(C)C
Properties
C8H16O
Molar mass 128.21
Appearance white crystalline [1]
Melting point 106–107 °C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

In chemistry, 3,3,4,4-tetramethyltetrahydrofuran or 3,3,4,4-tetramethyloxolane is a heterocyclic compound with the formula C
8H
16O, or (CH3)2((CH2)C2(CH2)O)(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 not adjacent to the oxygen. It can be seen also as a cyclic ether of 2,2,3,3-tetramethylbutane, an isomer of octane.

Synthesis and chemistry

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The compound can be prepared by heating 2,2,3,3-Tetramethylbutane-1,4-diol in dimethylsulfoxide at 160 °C.[1][2][3] The compound is decomposed by butyllithium with cleavage of the ring, and this reaction has been considered as a way of obtaining lithium enolates of aldehydes.[1][2]

In a superacid solution (SbF
5-HSO
3F-SO
2), the oxygen atom is protonated, and the carbon chain is split at the 3-4 bond, which gets replaced by bonds from carbons 3 and 4 to the oxygen atom. The formula of the resulting species could be written as (–(CH
3)2C-CH2–)2O+
H.[4]

See also

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References

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  1. ^ a b c d Kroposki, Lorraine Marie (1970) Retrocycloadditions of anions from tetrahydrofurans and hexahydrooxepin. Masters Thesis, University of Arizona.
  2. ^ a b R. B. Bates, L. M. Kroposki, D. E. Potter (1972), Cycloreversions of anions from tetrahydrofurans. Convenient synthesis of lithium enolates of aldehydes. Journal of Organic Chemistry, volume 37, issue 4, pages 560–562. doi:10.1021/jo00969a007
  3. ^ J. Bogner, J.-C. Duplan, Y. Infarnet, J. Delmau, J. Huet (1972), Conformational studies on methylated tetrahydrofurans. 1. Priori Determination Of Favored Conformers - NMR Study Of Conformation Equilibrium. Bulletin de la Société Chimique de France, 3616
  4. ^ Y. Infarnet, J. C. Duplan and 3. Huet (2005), Saturated 5-Membered Ring Conformation 1-lH NMR Study of Protonated Methyltetrahydrofurans in Superacid Medium. Organic Magnetic Resonance, volume 16, issue 1, pages 68–70. doi:10.1002/mrc.1270160119
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