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DOI: 10.1055/s-2006-951467
Preparation of (Z)-1-Halo-1-alkenes and (Z)-1-Halo-2-alkoxy-1-alkenes Using Cr(II/III) and Fe(0)
Publikationsverlauf
Publikationsdatum:
22. September 2006 (online)
Abstract
Reduction of 1,1,1-trihaloalkanes by Cr(II) or Cr(III) regenerated by Fe(0) in moist tetrahydrofuran at room temperature stereoselectively generates (Z)-1-halo-1-alkenes and (Z)-1-halo-2-alkoxy-1-alkenes in good to excellent yields.
Key words
alkenyl halides - carbenoids - chromium - enol ethers
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References and Notes
Spectral data for 18: 1H NMR (400 MHz, CDCl3): δ = 7.31-7.38 (m, 5 H), 6.63 (d, J = 4 Hz, 1 H), 5.13 (d, J = 4 Hz, 1 H), 4.93 (s, 2 H). 13C NMR (100 MHz, CDCl3): δ = 147.2, 136.6, 128.9, 128.5, 127.6, 83.5, 74.6. 20: 1H NMR (300 MHz, CDCl3): δ = 7.89 (ddd, J = 2, 2, 9 Hz, 2 H), 6.94 (ddd, J = 2, 2, 9 Hz, 2 H), 6.62 (d, J = 4 Hz, 1 H), 5.22 (d, J = 4 Hz, 1 H), 5.08 (s, 2 H), 3.86 (s, 3 H). 13C NMR (75 MHz, CDCl3): δ = 192.6, 164.3, 147.6, 130.5, 127.2, 114.2, 83.8, 74.0, 55.7.