Preparation of (Z)-1-Halo-1-alkenes and (Z)-1-Halo-2-alkoxy-1-alkenes Using Cr(II/III) and Fe(0)

J. R. Falck; Anyu He; Romain Bejot; Charles Mioskowski

doi:10.1055/s-2006-951467

LETTER

Preparation of (Z)-1-Halo-1-alkenes and (Z)-1-Halo-2-alkoxy-1-alkenes Using Cr(II/III) and Fe(0)

J. R. Falck*^a, Anyu He^a, Romain Bejot^b, Charles Mioskowski*^b
^a Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390-9038, USA
Fax: +1(214)6486455; e-Mail: j.falck@UTSouthwestern.edu;
^b Laboratoire de Synthèse Bio-Organique, UMR 7175, LC1, Faculté de Pharmacie, Université Louis Pasteur, 74 Route du Rhin, BP 24, 67 401 Illkirch, France
Fax: +33(3)90244306; e-Mail: mioskow@aspirine.u-strasbg.fr;

Abstract

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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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Referenzen

References and Notes

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<A NAME="RS11006ST-4">4</A> Mn(0) has been utilized previously to regenerate Cr(II): Fürstner A. Shi N. J. Am. Chem. Soc. 1996, 118: 12349

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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.