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TCI Practical Example: Construction of an Aziridine Ring

We are proud to present the construction of aziridine ring from alkene by using PhINTs and Cu(acac)₂.

Used Chemicals

• 1,2-Dihydronaphthalene [D0585]
• 4-Methyl-N-(phenyl-λ³-iodaneylidene)benzenesulfonamide (= PhINTs) [T3967]
• Bis(2,4-pentanedionato)copper(II) (= Cu(acac)₂) [C0384]
• Acetonitrile

Procedure

1,2-Dihydronaphthalene (360 mg, 2.77 mmol) and bis(2,4-pentanedionato)copper(II) (60 mg, 0.233 mmol) were added sequentially to a solution of PhINTs (866 mg, 2.32 mmol) in acetonitrile (15 mL) and the mixture was stirred at room temperature. After stirringed for 3 hours, the reaction mixture was filtered through, and the residue was washed with ethyl acetate (10 mL). The filtrate was concentrated under reduced pressure and the crude product was purified by silica gel column chromatography (hexane:ethyl acetate = 5:1) to afford N-tosyl-1,2,3,4-tetrahydronaphthalene-1,2-imine as a white solid (490 mg, 71% yield).

Experimenter's Comments

The reaction mixture was monitored by TLC (hexane:ethyl acetate = 2:1, Rf= 0.40).
The filtration residue was disposed of as copper waste.

Analytical Data

N-Tosyl-1,2,3,4-tetrahydronaphthalene-1,2-imine

¹H NMR (400 MHz, DMSO-d₆); δ 7.81 (d, J = 8.0 Hz, 2H), 7.30 (d, J = 8.2 Hz, 3H), 7.22-7.14 (m, 2H), 7.04 (d, J = 7.3 Hz, 1H), 3.81 (d, J = 7.0 Hz, 1H), 3.56-3.54 (m, 1H), 2.80-2.71 (m, 1H), 2.55-2.51 (m, 1H), 2.41 (s, 3H), 2.28-2.22 (m, 1H), 1.69-1.63 (m, 1H).

Other References

• Development of the Copper-Catalyzed Olefin Aziridination Reaction
  • D. A. Evans, M. T. Bilodeau, M. M. Faul, J. Am. Chem. Soc. 1994, 116, 2742.