1-Octene → 1-Octene

Participants

Reaction Steps

Reactions were carried out in a 100 ml three-necked flask fitted with a reflux condenser, thermometer and septum. The reflux condenser was connected to a cooling bath to ensure a constant flow of chilled water through the jacket, thereby preventing loss of octene. The top of the condenser was connected to a cold trap and bubbler in order to monitor liquid losses and gas emissions. The thermometer was positioned below the level of the reaction solution to ensure correct temperature monitoring. The reaction flask was purged with argon to ensure removal of oxygen. The reagents [EP or PCy3, RuCl3.xH2O and 1,4-butynedioldiacetate (BDD) and 1-octene)] were added to the flask under inert conditions, then a slow hydrogen sparge (2 bubbles per second) was started and maintained during the reaction. The reaction mixture was heated, with stirring, to the desired temperature. Samples were taken at regular intervals with a syringe through the septum and quenched with a mixture of toluene and two drops of t-butylhydroperoxide. Samples were analyzed by GC using a Pona column. Unless otherwise stated, 20 ml of octene was employed in all experiments, and catalyst, solvent and additive amounts were calculated relative to this. Octadecane in an amount of 0.5 ml was used as internal standard. The conversion percentages (as molar %) of 1-octene to 7-tetradecene are provided in FIGS. 1 and 2.

Provenance & Evidence