Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 9-10
139
Views
20
CrossRef citations to date
0
Altmetric
Original Articles

Reductions of Alkyl and Aryl Halides with Magnesium and Methanol

, , &
Pages 1519-1522 | Received 10 Nov 1988, Published online: 24 Oct 2006

References

  • Hutchins , R. O. , Suchismita Zipkin , R. E. , Taffer , I. M. , Sivakumar , R. , Monaghan , A. and Elisseou , E. M. in press . Tetrahedron Lett. ,
  • Youn , I. K. , Yon , G. H. and Pak , C. S. 1986 . Tetrahedron Lett. , 27 : 2409 Recent disclosures of the selective pi bond and other functional group reductions include: a. Conjugated esters;;Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G. ibid. 1987, 28, 5287; Hudlicky, T; Natchus, M. G.; Sinai-Zingde, G. J. Org. Chem. 1987, 52, 4641.
  • Zechmeister , L. and Rom , P. 1929 . Justus Liebigs Ann. Chem. , 468 : 117 Conjugated ketones (to saturated alcohols):
  • Profitt , J. A. , Watt , D. S. and Corey , E. J. 1975 . ibid. , 40 : 127 Conjugated nitriles:;Camps, P.; Ortuno, R. M.; Serratosa, F. Tetrahedron 1976, 32, 2583; Dinizo, S. E.; Freerksen, R. W.; Pabst, W. E.; Watt, D. S. J. Org. Chem. 1976, 41, 2846; Freerksen, R. W.; Pabst, W. E.; Raggio, M. L.; Sherman, S. A.; Wroble, R. R.; Watt, D. S. J. Amer. Chem. Soc. 1977, 99, 1536; Heissler, D.; Riehl, J.-J. Tetrahedron Lett. 1979, 3957; Geze, M.; Blanchard, P.; Fourrey, J. L.; Robert-Gero, M. J. Amer. Chem. Soc. 1983, 105, 7638; Freerksen, R. W.; Selikson, S. J.; Wroble, R. R.; Kyler, K. S.; Watt, D. S. J. Org. Chem. 1983, 48, 4087; Maity, S. K.; Mukherjee, D. Tetrahedron 1984, 40, 757; Kandil, A. A.; Slessor, K. N. J. Org. Chem. 1985, 50, 5649; Braish, T. F.; Fuchs, P. L. Syn. Commun. 1985, 15, 549; Garratt, P. J.; Doecke, C. W.; Weber, J. C.; Paquette, L. A. J. Org. Chem. 1986, 51, 449; Paquette, L. A.; Okazaki, M. E.; Caille, J.-C. ibid. 1988, 53, 477.
  • Brettle , R. and Shibib , S. M. 1981 . J. Chem. Soc., Perkin I , : 2912 Conjugated amides:;Ainscow, R. B.; Brettle, R.; Shibib, S. M. ibid. 1985, 1781; Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138.
  • Profett , J. A. and Ong , H. H. 1979 . ibid. , 44 : 3972 Diphenylethylenes:
  • Brown , A. C. and Carpino , L. A. 1985 . ibid. , 50 : 1749 Desulfonylation:
  • Zechmeister , L. and Rom , P. 1929 . Justus Liebigs Ann. Chem. , 468 : 117
  • Bryce-Smith , D. , Wakefield , B. J. and Blues , E. T. 1963 . Proc. Chem. Soc. , : 219 The use of magnesium and isopropanol in combination with decahy-dronaphthalene at elevated temperatures (80–150°C) has been shown to reduce halides to hydrocarbons; see, Bryce-Smith, D.; Wakefield, B. J. Org. Synth. 1973, IV, 998.

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.