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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 12
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Original Articles

Imine Anions Derived from 2° Allylic Amines

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Pages 1017-1024 | Published online: 05 Dec 2006

References

  • On leave, Institute of Elemento Organic Chemistry, Nankai University, Tientsin, Peoples' Republic of China 1980–1981
  • Seebach , D. and Geiss , K ‐H. 1976 . “ New Applications of Organometallic Reagents in Organic Synthesis ” . In Organometallic Chemistry Library 1 , Edited by: Seebach , D. 21 – 26 . Amsterdam : Elsevier Publishing Co. .
  • Still , W. C. and Macdonald , T. L. 1976 . J. Org. Chem. , 41 : 3620
  • Pohmakotr , M. , Geiss , K ‐H and Seebach , D. 1979 . Chem. Ber. , 112 : 1420
  • Geiss , K. H. , Seebach , D. and Seuring , B. 1977 . Chem. Ber. , 110 : 1833
  • Carlson , R. M. 1978 . Tetrahedron Lett. , 2 : 111
  • Carlson , R. M. , White , L. L. and Meyer , F. K. to be published
  • Martinez , S. J. and Toule , T. A. 1978 . Tetrahedron , 34 : 3027 The isomerization reported herein bears some similarity to the reported isomerization of 3° allylic amines to enamines, see, and references therein
  • Hänssgen , D. and Odenhauser , E. 1979 . Chem. Ber. , 112 : 2389 These results are in contrast to those observed with other 2° allyl amines which, depending on the reaction conditions, have been found to undergo addition or to form the vinyl amide dianion, see
  • Wender , P. A. and Schaus , J. M. 1978 . J. Org. Chem. , 43 : 782 and references therein
  • 20MHz C‐13 NMR: °c(ppm) 161
  • House , H. O. 1974 . Modern Synthetic Reactions , 2nd Ed. , 89 – 93 . New York , N. Y. : W. A. Benjamin Inc. . Prepared by the lithium aluminum hydride reduction of the formamide (optimum time‐4 hrs/ether) which, in turn, had been generated by refluxing the amine in a 10‐fold excess of ethyl formate. The products always indicated a certain amount of reduction of the double bond in a manner similar to that reported for allylic alcohols see:
  • Weston , A. W. , Ruddy , A. W. and Sater , C. M. 1943 . J. Amer. Chem. Soc. , 65 : 674 An independent synthesis was performed using the allylic sulfonamide anion and methyl iodide in a similar manner to that described by:
  • Wittig , G. and Suchanek , P. 1963 . Agnew, Chem. Int. Ed. , 2 : 683 m. p. 82–82°

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