1,3-dioxolane, formal glycol
3D model (Jmol)
|Molar mass||74.08 g/mol|
|Melting point||−95 °C (−139 °F; 178 K)|
|Boiling point||75 °C (167 °F; 348 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Dioxolane is a heterocyclic acetal with the chemical formula (CH2)2O2CH2. It is related to tetrahydrofuran by interchange of one oxygen for a CH2 group. The corresponding saturated 6-membered C4O2 rings are called dioxanes. The isomeric 1,2-dioxolane (wherein the two oxygen centers are adjacent) is a peroxide. 1,3-Dioxolane is used as a solvent and as a comonomer in polyacetals.
Dioxolanes as a class of compounds
Neosporol is a natural product that includes a 1,3-dioxolane moiety, and is an isomer of sporol which has a 1,3-dioxane ring. The total synthesis of both compounds has been reported, and each includes a step in which a dioxolane system is formed using trifluoroperacetic acid (TFPAA), prepared by the hydrogen peroxide – urea method. This method involves no water, so it gives a completely anhydrous peracid, necessary in this case as the presence of water would lead to unwanted side reactions.
In the case of neosporol, a Prilezhaev reaction with trifluoroperacetic acid is used to convert a suitable allyl alcohol precursor to an epoxide, which then undergoes a ring-expansion reaction with a proximate carbonyl functional group to form the dioxolane ring.
A similar approach is used in the total synthesis of sporol, with the dioxolane ring later expanded to a dioxane system.
- 1,3-Dioxolane at Sigma-Aldrich
- formal glycol - PubChem Public Chemical Database
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