A Novel Synthesis of 5-Perfluoroalkyl-2,3-dihydro-1,4-diazepines from 1-Perfluoroalkyl-2-iodoethylenes

Abstract

A novel method for the synthesis of 5-perfluoroalkyl-2,3-dihydro-1,4-diazepines using easily available starting materials is described. 1-Perfluoroalkyl-2-iodoethylenes, obtained from the reaction of perfluoroalkyl iodides and alkynes, reacted with ethylenediamine under mild conditions to give the title compounds in good yields. A possible mechanism is proposed.

Key words

perfluoroalkyl iodides - 1-perfluoroalkyl-2-iodoethylenes - 5-perfluoroalkyl-2,3-dihydro-1,4-diazepines - ethylenediamine

References

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13

X-ray data for compound 2g: C₁₂H₁₁ClF₂N_2, M = 256.68, triclinic, a = 11.3673(12) Å, b = 11.4429(12) Å, c = 11.4833(12) Å, V = 1191.9(2) ų, D_c = 11.430 g/cm³, crystal size: 0.486 × 0.272 × 0.138 mm. Data were measured at 293 K on a Bruker SMART CCD diffractometer with graphite monochromated Mo-K_α radiation.