Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 11
34
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Conjugate Addition of Alkyllithium Reagents to α,β-Unsaturated N, N',N'-Trimethylhydrazides

&
Pages 837-842 | Published online: 06 Dec 2006

References

  • Wakefield , B. J. 1974 . “The Chemistry of Organolithium Compounds” , 122 – 143 . New York : Pergamon Press .
  • Eicher , T. 1966 . “The Chemistry of Carbonyl Compounds” , Edited by: Patai , S. 624 – 631 . New York : Interscience Publishers .
  • Octanoic acid trimethylhydrazide, as an example, is inert to methyllithium in tetrahydrofuran solution at 25°
  • Meyers , A. I. and Whitten , C. E. 1976 . Tetrahedron Lett. , : 1947 – 1950 . For recent studies on electrophilic acrylate equivalents, see
  • Tamaru , Y. , Harada , T. , Iwamoto , H. and Yoshida , Y. 1978 . J. Amer. Chem. Soc. , 100 : 5221 – 5223 .
  • Corey , E. J. and Boger , D. 1978 . Tetrahedron Lett. , : 9 – 12 .
  • Baldwin , J. E. and Dupont , W. A. 1980 . Tetrahedron Lett. , : 1881
  • Class , J. B. , Aston , J. G. and Oakwood , T. S. 1953 . J. Amer. Chem. Soc. , 75 : 2937 – 2939 .
  • Paulsen , H. and Stoye , D. 1970 . “The Chemistry of Amides” , Edited by: Zabicky , J. 525 – 545 . New York : Interscience Publishers . For as summary of methods for preparation of hydrazides, see
  • Alkyllithium reagents were purchased from Ventron-Alfa: methyl-lithium-lithium bromide complex in ether, n-butyllithium in hexane, and t-butyllithium in pentane solution
  • Other solvents which were tried include hexane, toluene, ether, hexane/THF mixtures, glyme, and THF/hexamethylphosphoramide mixtures
  • Compounds 3a-d were prepared from the appropriate acid chloride and trimethylhydrazine following the procedure used for 1.
  • 96 – 105 . For a discussion see ref. 1a
  • Dreux , J. 1954 . Bull. Soc. Chim. Fr. , : 1309 – 1311 .

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.