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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 11-12
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Original Articles

Direct Formation and Reaction of Functionalized thienyl-Based Organocopper Reagents

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Pages 1833-1840 | Received 14 Mar 1989, Published online: 24 Oct 2006

References

  • Wu , T.-C. and Rieke , R. D. 1988 . Tetrahedron Lett. , 29 : 6753
  • Whemeyer , R. M. and Rieke , R. D. 1988 . Tetrahedron Lett. , 29 : 4513
  • Ebert , G. W. and Rieke , R. D. 1988 . J. Org. Chem. , 53 : 4482
  • Wu , T.-C. and Rieke , R. D. 1988 . J. Org. Chem. , 53 : 2381
  • Wu , T.-C. , Wehmeyer , R. M. and Rieke , R. D. 1987 . J. Org. Chem. , 52 : 5057
  • Wehmeyer , R. M. and Rieke , R. D. 1987 . J. Org. Chem. , 52 : 5056
  • Ebert , G. W. and Rieke , R. D. 1984 . J. Org. Chem. , 49 : 5280
  • Rieke , R. D. , Wehmeyer , R. M. , Wu , T.-C. and Ebert , G. W. 1989 . “Recent Developments in Organocopper Chemistry” Lipshutz, B. H., Ed.; Tetrahedron Symposia-in-print Number 35; . Tetrahedron , 45 : 443
  • Lithium 2-thienylcyanocuprate (0.25 M solution in THF) was purchased from Aldrich Chemical Company, Inc. We have received two different batches of lithium 2-thienylcyanocuprate during the period of this study. Lot no. 00921CV gave a very reactive copper without any difficulty. However, the other lot no. 04119KV was not able to produce reasonably reactive copper species.
  • Lipshutz , B. H. , Parker , D. A. , Kozlowski , J. A. and Nguyen , S. L. 1984 . Tetrahedron Lett. , 25 : 5959
  • Lipshutz , B. H. , Koerner , M. and Parker , D. A. 1987 . Tetrahedron Lett. , 28 : 945
  • Lipshutz , B. H. , Parker , D. A. , Nguyen , S. L. , McCarthy , K. E. , Barton , J. C. , Whitney , S. E. and Kotsuki , H. 1986 . Tetrahedron , 42 : 2873 and references cited therein.
  • Conjugate 1,4-addition reactions reported in this paper were not optimized and attempted using any additive such as BF3 etherate or chlorotrimethylsilane. These will be examined and addressed in the full paper later.

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