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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 6
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Original Articles

Nickel Catalyzed Alkylation of 2-Chloro-Pyridine. A Facile Synthesis of ω-(2-Pyridyl)-Alkylic Alcohols

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Pages 497-504 | Published online: 05 Dec 2006

References

  • Kumada , M. 1980 . Pure Appl. Chem. , 52 : 669 and refs. therein
  • The use of alkyl ether as protective group for -OH would be possible1 but drastic experimental conditions or expensive reagents would be required, at the end of the reaction, to remove the protective group
  • Rossi , R. 1977 . Synthesis , : 817
  • Decodts , G. , Dressaire , G. and Langlois , Y. 1979 . Synthesis , : 510
  • Dressaire , G. and Langlois , Y. 1980 . Tetrahedron Lett. , : 67
  • Our unpublished results; in the cross-coupling reaction on unprotected pbromophenol, using 2.2/1 mol Grignard reagent/mol halide, we have obtained only small quantities of alkylation products
  • Takei , H. , Miura , M. , Sugimura , H. and Okamura , H. 1979 . Chem. Lett. , : 1447
  • Pridgen , L. N. 1975 . J. Heterocyclic Chem. , 12 : 443
  • This solution was stored for 10 days, at -15°C, under N2 atmosphere
  • Houben-Weyl . 1973 . Methoden der Organischen Chemie , Vol. Band 13 , 113ff Stuttgart : G. Thieme Verlag . Teil 2a
  • Piccolo , O. , Consiglio , G. and Morandini , F. 1980 . Chimica e Industria , 62 : 69
  • Consiglio , G. , Morandini , F. and Piccolo , O. in preparation
  • Henrick , C. A. 1977 . Tetrahedron , 33 : 1845 and refs. therein
  • Green , N. , Jacobson , M. , Henneberry , T. J. and Kishaba , A. N. 1967 . J. Med. Chem. , 10 : 533
  • Eaton , P. E. , Cooper , G. F. , Johnson , R. C. and Mueller , R. H. 1972 . J. Org. Chem. , 37 : 1947
  • The b. ps. of (1-ethoxy)ethyl ether of 6-bromo-hexan-1-ol and 9-bromo-nonan-1-ol are 80°C (0.02 mm) and 102°C (0.5 mm) respectively

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