Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 8-9
50
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

The Birch Reduction - Dialkylation Reaction of Aromatic Carboxylic Acids. Identification of NaNH2 as the Base Responsible for the Second Alkylation

, &
Pages 1001-1012 | Received 22 Feb 1991, Published online: 23 Sep 2006

References

  • Harvey , R. G. 1970 . Synthesis , : 161
  • Birch , A. J. and Subba Rao , G. 1972 . “Advance in organic chemistry, methods and results” , Edited by: Taylor , E. C. Vol 8 , 1 – 65 . New York : Wiley-Interscience Publishers .
  • Bachi , M. D. , Epstein , J. W. , Herzberg-Minzil , Y. and Loewentahl , H. J. E. 1969 . J. Org. Chem. , 34 : 126
  • van Bekkum , H. , van den Bosch , C. B. , van Minnen-Pathuis , G. , de Mos , J. C. and van Wijk , A. M. 1971 . Rec. Trav. Chim. , 90 : 137
  • Saha , N. N. , Bagchi , P. N. and Dutta , P. C. 1955 . J. Am. Chem. Soc. , 77 : 3408
  • Piers , E. and Grierson , J. R. 1977 . J. Org. Chem. , 42 : 3755
  • Casares , A. , Cardoso , J. M. L. and Maldonado , L. A. 1981 . Synth. Commun. , 11 : 223
  • In this paper we will refer only to the identification of the base responsible for the alkylation at C-4 and hope to submit in other paper our experiments leading to the identification of the plyanion species involved
  • Peak area at δ 4.70 (A) = 3/5 diethyl product (3); therefore, (3) = 5/3 A. Peak area at δ 4.55 (B) = monoethyl product (2) + 2/5 diethyl product (3); therefore, (2) = B -2/5(5/3) A = B - 2/3 A
  • Kuehne , M. E. and Lambert , B. F. 1959 . J. Am. Chem. Soc. , 81 : 4278
  • Beverloo , A. , Dieleman , M. C. , Verkade , P. E. , De Vries , K. S. and Wepster , B. M. 1962 . Rec. Trav. Chim. , 81 : 1033
  • Jacobus , J. and Eastham , J. F. 1969 . Chem. Commun. , : 138

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.