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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 10
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Original Articles

Chemoselective Reduction of Vicinal-Dihalides with Mg-MeOH via SET

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Pages 1801-1809 | Received 03 Dec 1996, Published online: 22 Aug 2006

References & Notes

  • Hudlicky , T. , Zingde , G. S. and Natchus , M. G. 1987 . Tetrahedron Lett. , : 5287 I. K. Youn, G. H. Yon and C. S. Pak, ibid, 2409 (1986)
  • Profitt , J. A. , Watt , D. S. and Corey , E. J. 1975 . J. Org. Chem. , 40 : 127 R. Brettle and S. M. Shibib, J. Chem. Soc., Perkin Trans. I, 2912 (1981)
  • Profitt , J. A. and Ong , H. H. 1979 . J. Org. Chem. , 44 : 3972
  • Hutchins , R. O. , Suchismita , Zipkin , R. E. , Taffer , I. M. , Sivakumar , R. , Monaghan , A. and Elisseou , E. M. 1989 . Tetrahedron Lett. , 55
  • Dominguez , C. , Csaky , A. G. and Plumet , J. 1991 . Tetrahedron Lett. , : 4183
  • Hahn , W. E. and Lesiak , J. 1985 . Polish J. Chem. , 59 : 627
  • Maiti , S. N. , Spevak , P. and Reddy , A. V. N. 1988 . Synth. Commun. , : 1201
  • Kang , S.-K. , Kim , S.-G. , Park , D. C. , Lee , J.-S. , Yoo , W.-J. and Pak , C. S. 1993 . J. Chem. Soc., Perkin Trans. , I : 9
  • Pak , C. S. , Lee , E. and Lee , G. H. 1993 . J. Org. Chem. , 58 : 1523
  • Hutchins , R. O. , Suchismita , Zipkin , A. E. and Taffer , I. M. 1989 . Synth. Commun. , : 1519
  • A reaction of Z-stilbene with Mg-MeOH using 1:20 molar ratio of Z-stilbene to Mg at ambient temperature was monitored and showed the presence of bibenzyl only and no E-stilbene was detected at any stage.
  • The anti-alignment in meso-and dl-III, though favored by orbital symmetry rules, is opposed in the latter case conformationally by a energy difference of 4.4Kcal/mol; Fischer G. Muszkat K. A. Fisher E. J. Chem. Soc., B 1968 1156
  • Bunnett , J. F. 1978 . Acc. Chem. Res. , 11 : 413
  • Cyclohexene (96%) was recovered unchanged after 24 hr from its reaction with Mg-MeOH using 1: 10 molar ratio of cyclohexene: Mg.

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