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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 10
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Original Articles

A New Method for the Preparation of β-Hydroxy Nitriles: Transformation of 3-Bromo-2-isoxazolines to β-Hydroxy Nitriles by Treatment of Alkanethiolates

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Pages 1433-1439 | Received 11 Aug 1993, Published online: 23 Sep 2006

References

  • Kozikowski , A. P. 1984 . Chem. Res. , 17 : 410 and references therein
  • Kozikowski , A. P. and Adamczyk , M. 1983 . J. Org. Chem. , 48 : 366
  • Moersch , G. W. , Wittle , E. L. and Neuklis . 1967 . J. Org. Chem. , 32 : 1387
  • Wade , P. A. and Hinney , H. R. 1979 . J. Am. Chem. Soc. , 101 : 1319
  • Wade , P. A. and Bereznak , J. F. B. 1987 . J. Org. Chem. , 52 : 2973
  • Brandi , A. , De Sarlo , F. , Guarna , A. and Speroni , G. 1982 . Synthesis , 719
  • Huisgen , R. and Christl , M. 1973 . Chem. Ber. , 106 : 3291
  • Vyas , D. M. , Skonezny , P. M. , Jenks , T. A. and Doyle , T. W. 1986 . Tetrahedron Lett. , 27 : 3099
  • Bromo nitrile oxide was prepared “in situ”, from dibromoformaldoxime and solid sodium bicarbonate
  • Caldirola , P. , Ciancaglion , M. , De Amici , M. and De Micheli , C. 1986 . Tetrahedron Lett. , 27 : 4647
  • Uhm , M. Y. , Lee , Y. Y. , Goo , Y. M. and Kim , K. J. 1989 . Korean. Chem. Soc. , 33 : 673
  • Sodium alkanethiolates were prepared from alkanethiols by treating with sodium hydride
  • All the compounds prepared by this method gave good analytical data
  • 2d: 1H-NMR(CDCl3), δ, 2. 72(d, 2H, J, = 6. 18 Hz, CH2CN), 5. 00(t, 1H, J, = 6. 18 Hz, CHOH), 7. 37 (s, 5H, Ph); IR(neat), 3400, 2250, 1055, 755, 700 cm−1 2f: 1H-NMR(D2O), δ, 2. 72(d, 2H, J, = 6. 42 Hz, CH2CN), 3. 62(d, 2H, J, = 5. 60 Hz, CH2OH), 4. 00(m, 1H, CHOH); IR(neat), 3380, 2250, 1100, 1045 cm−1 2g: 1H-NMR(CDCl3, δ, 2. 71(d, 2H, J, = 6. 15 Hz, CH2, CN), 3. 65(d, 2H, J, = 5. 26 Hz, CH2Cl), 4. 20(m, 1H, CHOH); IR(neat), 3400, 2255, 1090 cm−1 2h: 1H-NMR(CDCl3), δ, 3. 18–3. 49(m, 3H, CHCN, CH2, 5. 27(d, 1H, J, = 5. 15 Hz, CHOH), 7. 33(m, 4H, Ph). IR(neat), 3400, 2245, 1105, 1100, 760 cm−1 2i: 1H-NMR(CDCl3), δ, 4. 03(d, 1H, J, = 5. 76 Hz, CHCN), 4. 97(d, 1H, J, = 5. 45 Hz, CHOH), 7. 29(s, 10H, Ph); IR(neat), 3450, 2245, 1050, 760, 700 cm−1

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