Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 13
95
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

FACILE STEREOSELECTIVE SYNTHESIS OF (E)- AND (Z)-ALLYL BROMIDES FROM THE BAYLIS-HILLMAN ADDUCTS USING MgBr2

Pages 2059-2062 | Received 14 Sep 2000, Published online: 09 Nov 2006

REFERENCES

  • Chavan , S. P. , Ethiraj , K. S. and Kamat , S. K. 1997 . Tetrahedron Lett. , 38 : 7415
  • Gruice , A. and Foucaud , A. New J. Chem. , 15 943
  • Buchholz , R. and Hoffmann , H. M.R. 1991 . Helv. Chim. Acta , 74 : 1213
  • Hoffmann , H. M.R. and Rabe , J. 1985 . J. Org. Chem. , 50 : 3849
  • Semmelhack , M. F. and Wu , E. S.C. 1976 . J. Am. Chem. Soc. , 98 : 3384
  • McFadden , H. G. , Harris , R. L.N. and Jenkins , C. L.D. 1989 . Aust. J. Chem. , 42 : 301
  • Ameer , F. , Drewes , S. E. , Houston-McMillan , M. S. and Kaye , P. T. 1985 . Trans 1 . J. Chem. Soc. Perkin , : 1143
  • Basavaiah , D. , Pandiaraju , S. and Padmaja , K. 1996 . Synlett. , 4 : 393
  • Basavaiah , D. , Bakthadoss , M. and Pandiaraju , S. 1998 . Chem. Commun. , : 1638 and references cited therein
  • Basavaiah , D. , Bhavani , A. K.D. , Pandiaraju , S. and Sarma , P. K.S. 1995 . Synlett. , 3 : 243
  • Hoffman , H. M.R. and Rabe , J. 1983 . Angew. Chem. Int. Ed. Engl. , 22 : 795
  • 12. Spectral data for 2a: 1H NMR (200 MHz, CDCl3): δ 3.85 (s, 3H), 4.36 (s, 2H), 7.33–7.57 (m, 5H), 7.84 (s, 1H); 13C NMR (50 MHz, CDCl3): δ 26.62, 52.38, 128.60, 128.86, 129.55, 134.12, 143.11, 166.43; IR (neat): 1705, 1620 cm−1
  • Spectral data for 4a: 1H NMR (200MHz, CDCl3): δ 4.19 (s, −CH2 protons, (Z)-isomer), 4.23 (d, −CH2 protons, J = 0.8 Hz, (E)-isomer) 7.23 (s, vinylic proton, (E)-isomer), 7.34 (s, vinylic proton, (Z)-isomer), 7.37–7.54 (m, 3H), 7.73–0.82 (m, 2H); 13C NMR (50MHz, CDCl3): δ 26.63, 32.70, 108.06, 117.03, 129.04, 129.23, 130.44, 131.39, 132.41, 146.47, 147.21 in these the signals at 26.63, 130.44, 147.21 are due to minor (Z)-isomer: IR (KBr): 2120, 1610 cm−1

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.