1,3-Cycloheptadiene

Chemical Properties

1,3-Cycloheptadiene is a highly flammable cycloalkene that occurs as a colorless clear liquid.

Uses

1,3-Cycloheptadiene was used in the preparation of enantiopure epoxy cycloheptenyl sulfones.

General Description

1,3-Cycloheptadiene is a 1,3-cycloalkadiene. Isomerization of highly strained (E,E)-1,3-cycloheptadiene was investigated through double bond rotation, and electrocyclic ring closure. [1,5] Sigmatropic hydrogen shifts in 1,3-cyclohepatdiene were studied by density functional calculations.

Purification Methods

Purify the diene by dissolving it in Et2O, washing with 5% HCl, H2O, drying (MgSO4), evaporating, and the residue is distilled under dry N2 through a semi-micro column (some foaming occurs) [Cope et al. J Am Chem Soc 79 6287 1957, UV: Pesch & Friess J Am Chem Soc 72 5756 1950]. [Beilstein 5 IV 390.]

References

[1] Qin, Changyong, et al. “Stability and Thermal Rearrangement of (E,E)-1,3-Cycloheptadiene and Trans-Bicyclo[3.2.0]Hept-6-Ene.” The Journal of Physical Chemistry A, 110 5, 2006, pp. 2034–38, https://doi.org/10.1021/jp054885i.
[1] Hess, B. Andes, and John E. Baldwin. “[1,5] Sigmatropic Hydrogen Shifts in Cyclic 1,3-Dienes.” Journal of Organic Chemistry, 67 17, 2002, pp. 6025–33, https://doi.org/10.1021/jo025917q.
[3] Manner, William L., et al. “Structures and Reactivities of Cycloheptane, Cycloheptene, 1,3-Cycloheptadiene, and Cycloheptatriene on Pt(111).” The Journal of Physical Chemistry B, 103 32, 1999, pp. 6752–63, https://doi.org/10.1021/jp990501a.