Benzophenone → 1-Decene

Participants

Reaction Steps

Solutions were prepared by dissolving all of the following in a total volume of 5 mL: (a) 32.7 mg of 1,2-dibromodecane, 18.3 mg of benzophenone and 10.0 mg of dodecane in acetonitrile(ACN)/methanol (15:85 v/v); (b) 24.2 mg 1,2-dibromodecane, 22.4 benzophenone and 10.0 mg dodecane in acetonitrile/2-propanol (15:85 v/v); (c) 22.7 mg 1,2-dibromodecane, 20.7 mg benzophenone and 10.0 mg dodecane in acetonitrile/propylsulfide (15:85 v/v); (d) 25.0 mg 1,2-dibromodecane, 21.5 mg benzophenone and 10.5 mg dodecane in acetonitrile/triethylamine (15:85 v/v). Two 2 mL aliquots of each solution were placed in quartz cells 7×7 mm2) and deaerated by bubbling oxygen-free nitrogen for 15 minutes. Samples were then irradiated at 350 nm using a photoreactor equipped with two RPR-350 lamps. Samples were rotated with a "merry-go-round" (to ensure that all samples received the same irradiation dose) and irradiated for 1.5 hours (methanol), 40 minutes (2-propanol), 30 minutes (propylsulfide) or 1 minute (triethylamine). A valerophenone solution (prepared as described above) was used as relative actinometer. Product (i.e. 1-decene) quantification and quantum yields were carried out as described above. Results are summarized in the table below. No 1-decene is formed (a) in the absence of benzophenone or (b) in the absence of the chain extender.

Provenance & Evidence