(E)-oct-4-ene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: p-Tolyl azide (0.113 g, 0.852 mmol), trans-4-octene (3.705 g, 33.0 mmol), and [(Me,EtTCPh)Fe(NCCH3)2](PF6)2 (0.0118 g, 0.0085 mmol) were used in the General Catalytic Reaction described above yielding 0.055 g, 30%. 1H NMR (CDCl3, 499.74 MHz): δ 7.02 (d, J=7.5 Hz, 2H), 6.80 (d, J=8.5 Hz, 2H), 2.28 (s, 3H), 2.03 (t, J=5.5 Hz, 2H), 1.62 (m, 2H), 1.53 (m, 4H), 1.10 (m, 2H), 0.96 (t, J=7.0 Hz, 6H) 13C NMR (CDCl3, 125.66 MHz): δ 148.10, 130.91, 129.36, 120.95, 44.99, 33.29, 21.11, 20.80, 14.18. GC/MS (m/z): 217.2. DART HR MS (m/z): [M+H]+218.1901 (found). C5H24N, 218.1909 (calcd). above yielding 0.055 g, 30%

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An example of an alkene compound produced by partially hydrogenating an alkyne compound in the presence of a hydrogenation catalyst containing a hydrogenation promoter and a reducing agent will be described. First, 37.8 mg (1.00 mmol) of NaBH4 was charged to a 100-mL glass autoclave which was equipped with a stirrer and whose periphery was kept at 30° C., and the autoclave was purged with argon gas. Subsequently, 10 mL of DMF, 1.47 mL (10 mmol) of 4-octyne, and 1.00 mL (Pd content=10 μmol) of the hydrogenation promoter (1) prepared in Example 1 were added to the autoclave under an argon atmosphere. A hydrogenation catalyst (1) composed of the hydrogenation promoter (1) and NaBH4 was prepared in the autoclave by this operation. The autoclave was connected to a hydrogen gas cylinder via a gas-introducing tube, and air in the introducing tube was purged with hydrogen at 2 atm three times. Subsequently, hydrogen at 8 atm was introduced into the autoclave, and the hydrogen was then discharged carefully until the pressure was decreased to 2 atm. This operation was repeated seven times. The hydrogen pressure was then increased to 8 atm, and the solution was vigorously stirred at 30° C. Thereby, hydrogenation reaction proceeded. The conversion rate and the selectivity of cis-4-octene in the product were determined by GC. A trans isomer (trans-4-octene), positional isomers (trans-3-octene, cis-2-octene, and the like), and an excessively hydrogenated product (octane) were produced as by-products. Table 4 shows the result of this example. The selectivity described in Table 4 represents the ratio of the amount of cis isomer to the sum of all the amounts of alkenes (a cis isomer, a trans isomer, and positional isomers) and an alkane produced. This definition is also used for Table 5 and thereafter. containing a hydrogenation promoter was equipped with a stirrer was kept at 30° C. the autoclave was purged with argon gas was prepared in the autoclave by this operation air in the introducing tube was purged with hydrogen at 2 atm three times Subsequently, hydrogen at 8 atm was introduced into the autoclave The hydrogen pressure was then increased to 8 atm Thereby, hydrogenation reaction