A Facile 1,2-Acetoxychlorination Reaction of Olefins by Using the N,N-Dimethylacetamide/Hydrogen Chloride/M-Chloroperbenzoic Acid (or Oxone) System

REFERENCES

• Iqbal , J. and Srivastava , R. R. 1991 . Tetrahedron , 47 : 3155 Qian, C. and Zhu, D., Synth. Commun., 1994, 24, 2203; Bhar, S. and Ranu, B. C., J. Org. Chem., 1995, 60, 745.
   Web of Science ®Google Scholar
• Newman , M. S. and Chen , C. H. 1973 . J. Am. Chem. Soc. , 95 : 278 Newman, M. S. and Chen, C. H., J. Org. Chem., 1973, 38, 1173; Newman, M. S. and Olson, D. R., J. Org. Chem., 1973, 38, 4203; Elsenbaumer, R. L. and Mosher, H. S., J. Org. Chem., 1979, 44, 600; White, R. E., Miller, J. P., Favreau, L. V., and Bhattacharyya, A., J. Am. Chem. Soc., 1986, 108, 6024; Kolb, H. C. and Sharpless, K. B., Tetrahedron, 1992, 48, 10515.
   Web of Science ®Google Scholar
• Braeunig , C. , Duschek , C. , Fiedler , H. , Hampel , M. , Pritzkow , W. and Schmidt , H. 1975 . J. Prakt. Chem. , 317 : 874 (Chem. Abstr., 1976, 84, 89497).
   Google Scholar
• Bodrikov , I. V. , Spiridonova , S. V. and Smolyan , Z. S. 1977 . Zh. Org. Khim. , 13 : 486 (Chem. Abstr., 1977, 87, 22090).
   Google Scholar
• Baeckvall , J. E. 1977 . Tetrahedron Lett. , 40 : 467
   Google Scholar
• Baeckvall , J. E. , Young , M. W. and Sharpless , K. B. 1977 . Tetrahedron Lett. , 40 : 3523
   Google Scholar
• Motohashi , S. and Satomi , M. 1983 . Chem. Pharm. Bull. , 31 : 1788
   Google Scholar
• Kim , J. N. , Kim , H. R. and Ryu , E. K. 1992 . Synth. Commun. , 22 : 2521 Kim, H. R., Kim, J. N., Park, H. J., and Ryu, E. K., Bull. Korean Chem. Soc., 1997, 75, 110.
   Web of Science ®Google Scholar
• Kim , H. R. , Jung , J. H. , Kim , J. N. and Ryu , E. K. 1990 . Synth. Commun. , 20 : 637 Kim, H. J., Kim, H. R., Kim, J. N., and Ryu, E. K., Bull. Korean Chem. Soc., 1990, 11, 184; Chung, K. H., Kim, K. M., Kim, J. N., and Ryu, E. K., Synth. Commun., 1991, 21, 1917.
   Web of Science ®Google Scholar
• Chung , K. H. , Kim , H. J. , Kim , H. R. and Ryu , E. K. 1990 . Synth. Commun. , 20 : 2991
   Web of Science ®Google Scholar
• 1H NMR Data of Products. 1-Acetoxy-2-chloro-1-phenylethane (Entry 1): 1H NMR (CDCl3) δ 2.12 (s, 3H), 3.60–3.82 (m, 2H), 5.95 (dd, J=4.85, 7.61 Hz, 1H), 7.35 (s, 5H). 1-Acetoxy-2-chlorocyclohexane (Entry 2): 1H NMR (CDCl3) δ 1.18–1.52 (m, 4H), 1.55–1.85 (m, 4H), 2.00 (s, 3H), 3.75 (dt, J=5.10, 9.72 Hz, 1H), 4.71 (dt, J=4.55, 9.10 Hz, 1H). 1-Acetoxy-2-chlorocycloheptane (Entry 2): 1H NMR (CDCl3) δ 1.45–1.96 (m, 10H), 2.03 (s, 3H), 4.02 (dt, J=3.88, 7.94 Hz, 1H), 4.95 (dt, J=3.87, 7.86 Hz, 1H). 2-Acetoxy-1-chlorohexane and 1-Acetoxy-2-chlorohexane (Entry 4): 1H NMR (CDCl3) δ 0.78–0.95 (m, 3H), 1.17–1.48 (m, 4H), 1.52–1.78 (m, 2H), 2.01 (s, 0.7H), 2.02 (s, 0.3H), 3.44–3.65 (m, 1.4H), 3.93–4.08 (m, 0.3H), 4.15 (m, 0.6H), 4.92–5.08 (m, 0.7H). 2-Acetoxy-1-chloro-3-(2-ethoxycarbonyloxyphenyl)propane (Entry 5): 1H NMR (CDCl3) δ 1.29 (t, J=7.27 Hz, 3H), 1.98 (s, 3H), 2.89–2.95 (m, 2H), 3.42 (dd, J=5.03, 11.79 Hz, 1H), 3.55 (dd, 4.43, 11.79 Hz, 1H), 4.26 (q, J=7.13 Hz, 2H), 5.12 (m, 1H), 7.05–7.26 (m, 4H). 1-Acetoxy-2-chloro-3-(2-ethoxycarbonyloxyphenyl)propane (Entry 5): 1H NMR (CDCl3) δ 1.29 (t, J=5.44 Hz), 2.00 (s, 3H), 2.95 (dd, J=7.53, 14.13 Hz, 1H), 3.08 (dd, J=5.87, 14.23 Hz, 1H), 4.12–4.28 (m, 5H), 7.09–7.28 (m, 4H). 2-Chloro-1,3-diacetoxy-1-phenylpropane (Entry 6): 1H NMR (CDCl3) δ 1.98 (s, 3H), 2.04 (s, 1H), 2.06 (s, 2H), 3.88–4.35 (m, 3H), 5.94 (d, J=6.28 Hz, 1H), 7.20–7.31 (m, 5H).
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