Tetrahydrofuran → HCID 178506712, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (50 ml of 1.53M heptane solution) was introduced into a previously dried and nitrogen purged 100 ml Pyrex-glass pressure tube equipped with a perforated crown cap over a self-sealing rubber gasket. After adjusting the temperature of this solution to -78° C., 20 ml of tetrahydrofuran and 8 ml of 1,3,5-cycloheptatriene (0.077 moles) were added. The solution turned red in color almost immediately after addition of the 1,3,5-cycloheptatriene. This reaction mixture was maintained at -78° C. for 15 minutes. The temperature was adjusted to 0° C. and the solution maintained at this temperature for one hour. During this period the solution became very dark in color. Dilution of 38 ml of this n-butylcycloheptadienyllithium solution with 279 ml of toluene gave a red-violet solution having a molarity of 0.1255 as determined by disulfide titration. This titration method is described in C. A. Uraneck, J. E. Burleigh, and J. W. Cleary, Analytical Chemistry 40, 327 (1968).

Provenance & Evidence